Efficient synthesis of the C(1)-C(11) fragment of the tedanolides. The nonaldol aldol process in synthesis

Org Lett. 2000 Jun 15;2(12):1669-72. doi: 10.1021/ol005675l.

Abstract

[reaction: see text] The nonaldol aldol process developed in our laboratories has been applied to the synthesis of a C(1)-C(11) fragment 22 of the novel macrocyclic cytotoxic agents tedanolide and 13-deoxytedanolide 1 and 2. The commercially available hydroxy ester 7 was converted in 24 steps into compound 22 using two nonaldol aldol reactions.

Publication types

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

MeSH terms

  • Antibiotics, Antineoplastic / chemical synthesis
  • Antibiotics, Antineoplastic / chemistry*
  • Lactones / chemical synthesis
  • Lactones / chemistry
  • Macrolides / chemical synthesis
  • Macrolides / chemistry*
  • Marine Biology
  • Molecular Structure

Substances

  • 13-deoxytedanolide
  • Antibiotics, Antineoplastic
  • Lactones
  • Macrolides
  • tedanolide