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ChemInform Abstract: Stereoselective Syntheses of (+)-Rhopaloic Acid A and (-)-ent- and (.+-.)-rac-Rhopaloic Acid A.

✍ Scribed by R. TAKAGI; A. SASAOKA; H. NISHITANI; S. KOJIMA; Y. HIRAGA; K. OHKATA


Publisher
John Wiley and Sons
Year
2010
Weight
36 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis


Stereoselective Syntheses of (+)-Rhopaloic Acid A and (-)-ent-and (Β±)-rac-Rhopaloic Acid A. -Total syntheses of natural rhopaloic acid (XIII), its enantiomer and racemate via successive homologation of farnesol (I) and cyclization to form the tetrahydropyran ring are described. The asymmetric synthesis is achieved by way of the Evans' asymmetric alkylation of mixed anhydride derived from carboxylic acid (II) and pivaloyl chloride using 4-benzyloxazolidinones as chiral auxiliaries. -(TAKAGI, R.; SASAOKA, A.;


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