Total synthesis of (+)-scyphostatin featuring an enantioselective and highly efficient route to the side-chain via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)

Chem Commun (Camb). 2010 Apr 7;46(13):2200-2. doi: 10.1039/b920261g. Epub 2010 Feb 23.

Abstract

(+)-Scyphostatin (1) was synthesized via (i) construction of a side-chain 3b of > or = 98% purity in 19% yield in eleven steps featuring ZACA reaction, Negishi coupling, and HWE olefination, (ii) an asymmetric synthesis of a fully protected core 4 from 10a, and (iii) a three-step assembly of 1 in 42% yield.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Amides / chemical synthesis*
  • Amides / chemistry
  • Catalysis
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Stereoisomerism
  • Zirconium / chemistry*

Substances

  • Alkenes
  • Amides
  • Pyrones
  • scyphostatin
  • Zirconium