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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.


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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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DIBAL = Diisobutylaluminum Hydride

Link


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PivCl = pivaloyl chloride = t-Bu-COCl

TBS-Cl = tert-Butyldimethylsilyl Chloride

DIBAL = Diisobutylaluminum Hydride

TPAP = Tetrapropylammonium Perruthenate

NMO = N-Methylmorpholine-N-oxide


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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.


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LiHMDS = Lithium Hexamethyldisilazide = LiN(SiMe3)2


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Julia Olefination

Link


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Diimide Reductions


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


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Weinreb Amide


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Weinreb Amide General


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LAB = Lithium amidotrihydroborate = LiH2NBH3


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TIPS = Triisopropylsilyl

PCC = Pyridinium Chlorochromate


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


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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.


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LiTMP = Lithium tetramethylpiperidide

DBB = Di-tert-butylbiphenyl

Boc = tert-butyloxycarbonyl = t-BuO-CO


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Birch Reduction


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Mechanism of the Birch Reduction


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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.


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


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Link


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TMO = trimethylamine-N-oxide

pTSA = p-toluenesulfonic acid


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DMP = Dess-Martin Periodinane


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LiBH4 is a somewhat stronger reducing agent than NaBH4

… But still safer than LiAlH4


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Horner-Emmons-Wadsworth Reaction


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Mechanism of the HEW Reaction


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Corey-Bakshi-Shibata Reduction


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