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Welwitindolinone Alkaloids Friday Problem Set Phanindra Venukadasula 10-14-11

Welwitindolinone Alkaloids Friday Problem Set Phanindra Venukadasula 10-14-11. Welwitindolinones. Isolated from lipophilic extract of Hapalosiphon welwitschii W. & G.S - a blue-green algae (cyanobacteria)

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Welwitindolinone Alkaloids Friday Problem Set Phanindra Venukadasula 10-14-11

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  1. Welwitindolinone AlkaloidsFriday Problem SetPhanindra Venukadasula10-14-11

  2. Welwitindolinones • Isolated from lipophilic extract of Hapalosiphon welwitschii W. & G.S - a blue-green algae (cyanobacteria) • Shows antifungal activity and reverses P-glycoprotein-mediated multiple-drug-resistance (MDR) ina vinblastine restane subline of a human ovarian adenocarcinoma line. • The lipophilic extract of Westiella intricata Borzi exhibits insecticidal activity against blowfly larvae. • Welwitindoline A isonitrile isolated from H. welwitschii accounts for fungicidal activity. • The MDR reversing and larvacidal activities are associated with N-Methylwelwitindolinone C isothiocyanate - major alkaloid in both algae. • 3-Hydroxywelwitindolinones and related ethers are isolated from terrestrial Fischerella muscicola (Thuret) Gomont and Fischerella major Gomont. • Except for welwitindolinone A all members of the family have common carbon framework with a characteristic bicyclo[4.3.1]decane ring system. (a) Stratmann, K.; Moore, R. E.; Bonjouklian, R.; Deeter, J. B.; Patterson, G. M. L.; Shaffer, S.; Smith, C. D.; Smitka, T. A. J. Am. Chem. Soc.1994, 116, 9935–9942. (b) Jimenez, J. I.; Huber, U.; Moore, R. E.; Patterson, G. M. L. J. Nat. Prod.1999, 62, 569–572.

  3. Welwitindolinone Alkaloids (a) Stratmann, K.; Moore, R. E.; Bonjouklian, R.; Deeter, J. B.; Patterson, G. M. L.; Shaffer, S.; Smith, C. D.; Smitka, T. A. J. Am. Chem. Soc.1994, 116, 9935–9942. (b) Jimenez, J. I.; Huber, U.; Moore, R. E.; Patterson, G. M. L. J. Nat. Prod.1999, 62, 569–572.

  4. Biogenesis of Indole Alkaloids Stratmann, K.; Moore, R. E.; Bonjouklian, R.; Deeter, J. B.; Patterson, G. M. L.; Shaffer, S.; Smith, C. D.; Smitka, T. A. J. Am. Chem. Soc.1994, 116, 9935–9942.

  5. Proposed biosynthesis of N-methylwelwitindolinone D isonitrile Unlikely as chloroepoxides require relatively high temp’s to Rearrange to -chloroketones Jimenez, J. I.; Huber, U.; Moore, R. E.; Patterson, G. M. L. J. Nat. Prod.1999, 62, 569–572.

  6. Rawal: Retrosynthesis Bhat, V.; Allan, K. M.; Rawal, V. H. J. Am. Chem. Soc. 2011, 133, 5798–5801.

  7. Rawal: Forward Synthesis Zayia’s reagent

  8. Rawal: Synthesis of tetracyclic core Muratake, H.; Nakai, H. Tetrahedron Lett.1999, 40, 2355. Kawatsura, M.; Hartwig, J. F. J. Am .Chem. Soc. 1999, 121, 1473.

  9. enolate arylation Lloyd-Jones, G. C. Angew. Chem. Int., Ed.2002, 41, 953–955.

  10. Rawal: Endgame

  11. Formation of isothiocyanates from aldoximes Kim, J. N.; Jung, K. S.; Lee, H. J.; Soon, J. S. Tetrahedron Lett.1997, 38, 1597–1598.

  12. Baran: Retrosynthetic analysis Baran, P. S.; Richter, J. M. J. Am. Chem. Soc. 2005, 127, 15394–15396.

  13. Baran: Forward synthesis

  14. Direct C-C bond formation

  15. Baran: Forward Synthesis

  16. Baran: Endgame

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