Concise syntheses of (+)-macrosphelides A and B

  • Paek, SM; 
  • Seo, SY; 
  • Kim, SH; 
  • Jung, JW; 
  • Lee, YS; 
  • 외 2명
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초록

Unified and highly convergent total syntheses of (+)-macrosphelides A and B are described. Key features of the syntheses include (1) concise synthesis of the optically active delta-hydroxy-y-keto alpha,beta-unsaturated acid fragment via the direct addition of a trans-vinylogous ester anion equivalent to the readily available Weinreb amide and (2) facile construction of the 16-membered macrolide core of the macrosphelide series via an intramolecular nitrile-oxide cycloaddition (INOC).

키워드

CELL-CELL ADHESION; MACROSPHELIDE-A; ABSOLUTE STEREOSTRUCTURES; (+)-BREFELDIN-A; ESTERIFICATION; INHIBITORS; MACROLACTONIZATION; REDUCTION; MOLECULE; STRATEGY
제목
Concise syntheses of (+)-macrosphelides A and B
저자
Paek, SM; Seo, SY; Kim, SH; Jung, JW; Lee, YS; Jung, JK; Suh, YG
DOI
10.1021/ol0508429
발행일
2005-07-21
유형
Article
저널명
Organic Letters
권
7
호
15
페이지
3159 ~ 3162