Slide1 l.jpg
This presentation is the property of its rightful owner.
Sponsored Links
1 / 63

Luche Reduction PowerPoint PPT Presentation

  • Uploaded on
  • Presentation posted in: General

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.

Download Presentation

Luche Reduction

An Image/Link below is provided (as is) to download presentation

Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author.While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server.

- - - - - - - - - - - - - - - - - - - - - - - - - - E N D - - - - - - - - - - - - - - - - - - - - - - - - - -

Presentation Transcript

Slide1 l.jpg

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 l.jpg

Luche Reduction

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



Slide6 l.jpg

DIBAL = Diisobutylaluminum Hydride


Slide14 l.jpg

PivCl = pivaloyl chloride = t-Bu-COCl

TBS-Cl = tert-Butyldimethylsilyl Chloride

DIBAL = Diisobutylaluminum Hydride

TPAP = Tetrapropylammonium Perruthenate

NMO = N-Methylmorpholine-N-oxide

Slide15 l.jpg

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.

Slide16 l.jpg

LiHMDS = Lithium Hexamethyldisilazide = LiN(SiMe3)2

Slide17 l.jpg

Julia Olefination


Slide19 l.jpg

Diimide Reductions

Slide20 l.jpg

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

Slide21 l.jpg

Weinreb Amide

Slide22 l.jpg

Weinreb Amide General

Slide23 l.jpg

LAB = Lithium amidotrihydroborate = LiH2NBH3

Slide25 l.jpg

TIPS = Triisopropylsilyl

PCC = Pyridinium Chlorochromate

Slide27 l.jpg

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

Slide29 l.jpg

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 l.jpg

LiTMP = Lithium tetramethylpiperidide

DBB = Di-tert-butylbiphenyl

Boc = tert-butyloxycarbonyl = t-BuO-CO

Slide34 l.jpg

Birch Reduction

Slide35 l.jpg

Mechanism of the Birch Reduction

Slide36 l.jpg

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.

Slide39 l.jpg

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

Slide42 l.jpg


Slide43 l.jpg

TMO = trimethylamine-N-oxide

pTSA = p-toluenesulfonic acid

Slide44 l.jpg

DMP = Dess-Martin Periodinane

Slide56 l.jpg

LiBH4 is a somewhat stronger reducing agent than NaBH4

… But still safer than LiAlH4

Slide59 l.jpg

Horner-Emmons-Wadsworth Reaction

Slide60 l.jpg

Mechanism of the HEW Reaction

Slide62 l.jpg

Corey-Bakshi-Shibata Reduction

  • Login