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Jung, Michael E.; Im, G-Yoon J. Convergent total synthesis of the racemic HIF-1 inhibitor laurenditerpenol. Tetrahed - 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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slide1

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

slide3

Luche Reduction

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

Link

Link

slide14

PivCl = pivaloyl chloride = t-Bu-COCl

TBS-Cl = tert-Butyldimethylsilyl Chloride

DIBAL = Diisobutylaluminum Hydride

TPAP = Tetrapropylammonium Perruthenate

NMO = N-Methylmorpholine-N-oxide

slide15

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.

slide20

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

slide25

TIPS = Triisopropylsilyl

PCC = Pyridinium Chlorochromate

slide29

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.

slide33

LiTMP = Lithium tetramethylpiperidide

DBB = Di-tert-butylbiphenyl

Boc = tert-butyloxycarbonyl = t-BuO-CO

slide36

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.

slide43

TMO = trimethylamine-N-oxide

pTSA = p-toluenesulfonic acid

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