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Luche Reduction PowerPoint PPT Presentation


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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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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


DIBAL = Diisobutylaluminum Hydride

Link


PivCl = pivaloyl chloride = t-Bu-COCl

TBS-Cl = tert-Butyldimethylsilyl Chloride

DIBAL = Diisobutylaluminum Hydride

TPAP = Tetrapropylammonium Perruthenate

NMO = N-Methylmorpholine-N-oxide


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.


LiHMDS = Lithium Hexamethyldisilazide = LiN(SiMe3)2


Julia Olefination

Link


Diimide Reductions


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


Weinreb Amide


Weinreb Amide General


LAB = Lithium amidotrihydroborate = LiH2NBH3


TIPS = Triisopropylsilyl

PCC = Pyridinium Chlorochromate


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


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.


LiTMP = Lithium tetramethylpiperidide

DBB = Di-tert-butylbiphenyl

Boc = tert-butyloxycarbonyl = t-BuO-CO


Birch Reduction


Mechanism of the Birch Reduction


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.


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


Link


TMO = trimethylamine-N-oxide

pTSA = p-toluenesulfonic acid


DMP = Dess-Martin Periodinane


LiBH4 is a somewhat stronger reducing agent than NaBH4

… But still safer than LiAlH4


Horner-Emmons-Wadsworth Reaction


Mechanism of the HEW Reaction


Corey-Bakshi-Shibata Reduction


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