Total synthesis of (+)-przewalskin B

J Org Chem. 2011 Aug 19;76(16):6918-24. doi: 10.1021/jo201111w. Epub 2011 Jul 26.

Abstract

An efficient strategy for the total synthesis of (+)-przewalskin B is reported. The key steps feature an intermolecular S(N)2' substitution of iodoallylic phosphate with organocupper reagent, a diastereoselective organocatalytic aldol cyclization, as well as a Rh(2)(OAc)(4)-mediated intramolecular carbene insertion to the tertiary C-H bond.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Copper / chemistry*
  • Cyclization
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Indicators and Reagents / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Diterpenes
  • Indicators and Reagents
  • Przewalskin B
  • Copper