Iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans: application to concise construction of C28-C37 bicyclic core of (+)-sorangicin A

Chemistry. 2010 Feb 15;16(7):2072-8. doi: 10.1002/chem.200902999.

Abstract

A novel iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans have been achieved from delta-hydroxy alpha,beta-unsaturated aldehydes by treating with allyltrimethyl silane in THF at room temperature with good to excellent yields. This methodology has been successfully implemented for a concise asymmetric synthesis of C28-C37 dioxabicyclo[3.2.1]octane ring system of (+)-sorangicin A in 8 steps with 21% overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoglycosides / chemical synthesis*
  • Aminoglycosides / chemistry
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Catalysis
  • Cyclization
  • Iodine / chemistry*
  • Molecular Structure
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry
  • Stereoisomerism

Substances

  • Aminoglycosides
  • Bridged Bicyclo Compounds
  • Pyrans
  • sorangicin A
  • Iodine