Total Synthesis of (+)-Elemol by Photoannelation

Published

Journal Article

A total synthesis of the monocyclic sesquiterpene elemol has been accomplished in seven steps and 16.7% overall yield. The key new carbon-carbon bonds were formed by the [2 + 2] photochemical cycloaddition reaction between 2,2,6-trimethyl-4H-1,3-dioxin-4-one and α-terpineol, a reaction that occurred with essentially complete regioselectivity (head/head) and good alkene face selectivity (3.35/1). The 35-38% enantiomeric purity of the starting (-)-α-terpineol was translated into optically active elemol predominating in the unnatural (+) enantiomer (ee = 31-40%). © 1985, American Chemical Society. All rights reserved.

Full Text

Duke Authors

Cited Authors

  • Baldwin, SW; Martin, GF; Nunn, DS

Published Date

  • January 1, 1985

Published In

Volume / Issue

  • 50 / 26

Start / End Page

  • 5720 - 5723

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo00350a055

Citation Source

  • Scopus