ChemInform Abstract: Total Synthesis of (+)-3-Oxacarbacyclin. Part 1. Retrosynthesis and Asymmetric Olefination Through Horner—Wadsworth—Emmons, Peterson and Martin Reactions.

✍ Scribed by H.-J. GAIS; G. SCHMIEDL; R. K. L. OSSENKAMP

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 43 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199811257

✦ Synopsis

Total Synthesis of (+)-3-Oxacarbacyclin. Part 1. Retrosynthesis and Asymmetric Olefination Through Horner-Wadsworth-Emmons, Peterson and Martin Reactions.

-The Horner-Wadsworth-Emmons reaction of the ketones (I) and (V) with the phosphonates (II), (VI), and (IXb), the Peterson reaction of (V) with the silicon compound (IXa), and the Martin reaction to the esters (XIV) and (XV) are studied intensively, because they can be used as key step in the total synthesis of (+)-3-oxacarbacyclin. The stereochemistry can be explained by a high substrate and auxiliary-induced facial selectivity. Interestingly, all reactions involving 8-phenylmenthol as chiral auxiliary proceed with the same asymmetric induction.

-(GAIS, H.-J.;