Total synthesis of (±)-hippolachnin A

Angew Chem Int Ed Engl. 2015 Feb 16;54(8):2378-82. doi: 10.1002/anie.201410419. Epub 2014 Dec 4.

Abstract

The first total synthesis of the marine polyketide (±)-hippolachnin A has been achieved in nine linear steps and an overall yield of 9%. Rapid access to the oxacyclobutapentalene core structure was secured by strategic application of an ene cyclization.

Keywords: ene reaction; hippolachnin A; natural products; photochemistry; total synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Coordination Complexes / chemistry
  • Cyclization
  • Cyclobutanes / chemistry
  • Cyclopentanes / chemistry
  • Kinetics
  • Polyketides / chemical synthesis*
  • Polyketides / chemistry
  • Rhodium / chemistry
  • Stereoisomerism
  • Thermodynamics

Substances

  • Coordination Complexes
  • Cyclobutanes
  • Cyclopentanes
  • Polyketides
  • hippolachnin A
  • pentalenene
  • Rhodium