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Zaragozic Acids:

Zaragozic Acids:. Literature Meeting Presented by Kimberly-Ann Laberge April 17, 2007. Synthesis of Core, Side Chains and Total Synthesis of the Zaragozic Acid A and C. Zaragozic Acids. Sooty Blotch = Leptodontium elastius.

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Zaragozic Acids:

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  1. Zaragozic Acids: Literature Meeting Presented by Kimberly-Ann Laberge April 17, 2007 Synthesis of Core, Side Chains and Total Synthesis of the Zaragozic Acid A and C

  2. Zaragozic Acids Sooty Blotch = Leptodontium elastius • Characterized by a 4,6,7-trihydroxy-2,8-dioxabicyclo[3,2,1]octane-3,4,5-tricarboxylic acid core with an array of six stereogenic centers including contiguous quaterny ones, with various C1 alkyl and the C6 O-acyl side chains. • Zaragozic Acid A was extracted from an unidentified sterile fungal culture, Sporormiella intermedia, and Zaragozic Acid B and C from a fungal strain, Leptodontium elatius. • Class of Natural Products that have been shown to be potent inhibitor of both squalene synthase, an enzyme found in the cholestrol biosynthetic pathway, and farnesyl-protein transferase(FPTase), a potential target enzyme in the treatment of cancer.

  3. Family of Zaragozic Acids .Nicolaou (Dihydroxylation Strategy) .Carreira (Carbonyladdition Strategy) .Evans (Tartrate-Derived Aldol Strategy)

  4. Outline • Total Synthesis of Zaragozic Acid: .A: Nicolaou -Synthesis of the Side Chains .C. Carreira -Synthesis of the Side Chains .C: Evans

  5. Nicolaou’s Retrosynthesis Addition of the C6 O-AcylSide Chain Addition of the C1 Akyl Side Chain Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  6. Nicolaou’s Retrosynthesis Dihydroxylation StilleCoupling Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  7. Synthesis of the C1 Akyl Side Chain Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  8. Synthesis of the C1 Akyl Side Chain >95:5 Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  9. Synthesis of the C1 Akyl Side Chain Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  10. Synthesis of the C1 Akyl Side Chain Recrystallisation for cyclohexane to give 95% ee 8% overallyield in 10 stepsfrom 4 (allylicalcohol) C1 Alkyl Side Chain Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  11. Synthesis of C6 O-Acyl Side Chain 92% de C6 O-AcylSide Chain Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  12. Stille Coupling Organostannate R-Halide Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  13. Stille Coupling Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  14. 1st Assymetric Dihydroxylation β-face Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656. α-face

  15. 2nd Assymetric Dihydroxylation Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  16. Functionalization Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  17. Functionalization Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  18. Dithiane Addition – 1st Attempt Undesired Product Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  19. Dithiane Addition – 2nd Attempt Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  20. Rearrangement Cascade Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  21. Dithiane Addition – 3rd Attempt Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  22. Rearrangement Cascade Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  23. Coupling of the Side Chain Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  24. Completion of the Total Synthesis ZaragozicAcid A Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  25. Nicolaou’s Total Synthesis Summary Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F.; Nicolaou, K.C. Chem. Eur. J. 1995, 1, 467-494. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  26. Carreira’s Retrosythesis Addition of C6 sidechain Ketalisation Addition of C1 sidechain Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  27. Synthesis of the C1 Akyl Side Chain Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  28. Synthesis of the C1 akyl chain C1 Akyl Chain Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  29. Synthesis of C6 O-Acyl Side Chain >95% ee 60:40 mixture Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  30. Synthesis of C6 O-Acyl Side Chain C6 O-Acyl Side Chain Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  31. Carbonyl Addition 20:1 Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  32. Addition of the C1 Alkyl Chain Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  33. Functionalization Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  34. Ketalizaton Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  35. Functionalization Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  36. Towards Zaragozic Acid C Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  37. 1st Method Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  38. 1st Method Cont’d Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  39. 1st Method Cont’d Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  40. 2nd Method Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  41. 2nd Method Cont’d Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  42. Towards Zaragozic Acid C Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  43. Addition of the C6 O-Acyl Side Chain If coupling of the C6 sidechainwasdone on 50, the hydroxyl groups free at C6 and C7 position, a 1:3 mixture of C6:C7 (+)-Zaragozic Acid C Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  44. Carreira’s Total Synthesis Summary • Highlydiastereoselective addition of the Grignard to an unsaturatedketone: • + effect of Cosolvant and additive • -Use of [Cr(OAc)2.H2O]2 for stereoselectivereduction • -Regiselective protection of the C7 carbinol vs the C6 OH • -Installation of 3 aldehydessimultaneously (more efficient) Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1994,116, 10825-10826. , Du Bois, J.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 8106-8125. Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  45. Evans’s Retrosynthesis Esterification ZaragozicAcid C Ketalisation Addition Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M.; Evans, D. A. J. Am. Chem. Soc. 1994,116, 12111-12112 . Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  46. Evans’s Retrosynthesis Mukaiyama Aldol Reaction Evan’s Aldol Reaction Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M.; Evans, D. A. J. Am. Chem. Soc. 1994,116, 12111-12112 . Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  47. Evans Aldol Reaction Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M.; Evans, D. A. J. Am. Chem. Soc. 1994,116, 12111-12112 . Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  48. Mukaiyama Aldol Reaction Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M.; Evans, D. A. J. Am. Chem. Soc. 1994,116, 12111-12112 . Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  49. Functionalization >10:1 Correct C5 Dia Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M.; Evans, D. A. J. Am. Chem. Soc. 1994,116, 12111-12112 . Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

  50. Functionalization Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M.; Evans, D. A. J. Am. Chem. Soc. 1994,116, 12111-12112 . Koert, U. Angew. Chem. Int. Ed. Engli. 1995, 34, 773-778., Nadin, A.; Nicolaou, K.C. Angew. Chem . Int. Ed. Engl. 1996, 35, 1622-1656.

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