Total Synthesis of (+)-Elemol by Photoannelation
Journal Article (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