A short and convenient chemical route to optically pure 2-methyl chromanmethanols. Total asymmetric synthesis of beta-, gamma-, and delta-tocotrienols

J Org Chem. 2007 Aug 31;72(18):6735-41. doi: 10.1021/jo0705418. Epub 2007 Aug 9.

Abstract

With use of inexpensive commercially available raw materials, chromanmethanol precursors to the natural beta-, gamma-, and delta-tocotrienols have been prepared in high yield. Enzymatic resolution afforded chiral chromanmethanols in high enantiomeric excess. Subsequent attachment of the farnesyl side chain was high yielding, thus allowing the preparation of asymmetric beta-, gamma-, and delta-tocotrienols in one final step wherein simultaneous deprotection of the phenol and removal of the sulfone group occurs. This chemistry provides the first synthesis of natural-series beta-tocotrienol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromans / chemical synthesis
  • Chromans / chemistry*
  • Methanol / chemistry*
  • Methylation
  • Molecular Structure
  • Stereoisomerism
  • Vitamin E / analogs & derivatives*
  • Vitamin E / chemical synthesis
  • Vitamin E / chemistry

Substances

  • Chromans
  • Vitamin E
  • tocotrienol, delta
  • plastochromanol 8
  • tocotrienol, beta
  • Methanol