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Luche Reduction

Jung, Michael E.; Im, G-Yoon J. Convergent total synthesis of the racemic HIF-1 inhibitor laurenditerpenol. Tetrahedron Letters (2008), 49(33), 4962-4964. Luche Reduction. CeCl3 promotes the 1,2 reduction of a , b -unsaturated ketones, over the conjugate (1,4) reduction. Link Link.

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Luche Reduction

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  1. Jung, Michael E.; Im, G-Yoon J. Convergent total synthesis of the racemic HIF-1 inhibitor laurenditerpenol. Tetrahedron Letters (2008), 49(33), 4962-4964.

  2. Luche Reduction CeCl3 promotes the 1,2 reduction of a,b-unsaturated ketones, over the conjugate (1,4) reduction. Link Link

  3. DIBAL = Diisobutylaluminum Hydride Link

  4. PivCl = pivaloyl chloride = t-Bu-COCl TBS-Cl = tert-Butyldimethylsilyl Chloride DIBAL = Diisobutylaluminum Hydride TPAP = Tetrapropylammonium Perruthenate NMO = N-Methylmorpholine-N-oxide

  5. Ley, Steven V.; Norman, Joanne; Griffith, William P.; Marsden, Stephen P. Tetrapropylammonium perruthenate, Pr4N+RuO4-, TPAP: a catalytic oxidant for organic synthesis. Synthesis (1994), (7), 639-66.

  6. LiHMDS = Lithium Hexamethyldisilazide = LiN(SiMe3)2

  7. Julia Olefination Link

  8. Diimide Reductions

  9. Boukouvalas, John; Wang, Jian-Xin. Structure Revision and Synthesis of a Novel Labdane Diterpenoid from Zingiber ottensii. Organic Letters (2008), 10(16), 3397-3399.

  10. Weinreb Amide

  11. Weinreb Amide General

  12. LAB = Lithium amidotrihydroborate = LiH2NBH3

  13. TIPS = Triisopropylsilyl PCC = Pyridinium Chlorochromate

  14. TFEF = 2,2,2-trifluoroethyl formate = HCO2CH2CF3

  15. Donohoe, Timothy J.; Thomas, Rhian E.; Cheeseman, Matthew D.; Rigby, Caroline L.; Bhalay, Gurdip; Linney, Ian D. Flexible Strategy for the Synthesis of Pyrrolizidine Alkaloids. Organic Letters (2008), 10(16), 3615-3618.

  16. LiTMP = Lithium tetramethylpiperidide DBB = Di-tert-butylbiphenyl Boc = tert-butyloxycarbonyl = t-BuO-CO

  17. Birch Reduction

  18. Mechanism of the Birch Reduction

  19. However, the original Birch reduction conditions have some drawbacks, one of which is the use of liquid ammonia as solvent. The use of other electron donating reagents can permit the use of THF as solvent.

  20. Red-Al is less oxygen sensitive and more soluble than LiAlH4.

  21. Link

  22. TMO = trimethylamine-N-oxide pTSA = p-toluenesulfonic acid

  23. DMP = Dess-Martin Periodinane

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