The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the AB-spiroacetal segment

Org Biomol Chem. 2005 Jul 7;3(13):2399-409. doi: 10.1039/b504146e. Epub 2005 May 24.

Abstract

The convergent synthesis of the C1-C15 AB-spiroacetal subunit of altohyrtin A/spongistatin 1 is described. This highly stereocontrolled synthesis relies on matched boron aldol reactions of chiral methyl ketones, under Ipc(2)BCl mediation, to establish the C5, C9 and C11 stereocentres, and formation of the desired thermodynamic spiroacetal under acidic conditions. The scalable synthetic sequence developed provided access to multi-gram quantities of , thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetals / chemical synthesis
  • Alcohols / chemistry
  • Antineoplastic Agents / chemical synthesis*
  • Boron / chemistry
  • Ketones / chemistry
  • Macrolides / chemical synthesis*
  • Molecular Structure
  • Spiro Compounds / chemical synthesis
  • Stereoisomerism
  • Thermodynamics

Substances

  • Acetals
  • Alcohols
  • Antineoplastic Agents
  • Ketones
  • Macrolides
  • Spiro Compounds
  • spongistatin 1
  • Boron