Total synthesis of cribrostatin IV: fine-tuning the character of an amide bond by remote control

J Am Chem Soc. 2005 Apr 6;127(13):4596-8. doi: 10.1021/ja050203t.

Abstract

We report the enantioselective total synthesis of cribrostatin IV (1). Key features of this synthesis involve the convergent coupling of two highly functionalized homochiral components followed by a "lynchpin" Mannich cyclization to establish the pentacyclic core (cf. 19 --> 20).

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amides / chemical synthesis
  • Amides / chemistry
  • Animals
  • Isoquinolines / chemical synthesis*
  • Porifera / chemistry

Substances

  • Amides
  • Isoquinolines
  • cribrostatin 4