Efficient generation of ortho-quinone methide: application to the biomimetic syntheses of (±)-schefflone and tocopherol trimers

Daohong Liao; Houhua Li; Xiaoguang Lei

doi:10.1021/ol202641y

Efficient generation of ortho-quinone methide: application to the biomimetic syntheses of (±)-schefflone and tocopherol trimers

Org Lett. 2012 Jan 6;14(1):18-21. doi: 10.1021/ol202641y. Epub 2011 Nov 2.

Authors

Daohong Liao¹, Houhua Li, Xiaoguang Lei

Affiliation

¹ School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.

PMID: 22047096
DOI: 10.1021/ol202641y

Abstract

An efficient method using silver oxide-mediated oxidation for the synthesis of ortho-quinone methides has been developed and applied to the biomimetic syntheses of novel trimeric natural products, (±)-schefflone and tocopherol trimers. Further studies of the critical trimerization as well as substrate scope and limitations are also reported.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Biomimetic Materials / chemical synthesis*
Indolequinones / chemistry*
Molecular Structure
Monoterpenes / chemistry*
Oxidation-Reduction
Tocopherols / chemistry*

Substances

Indolequinones
Monoterpenes
schefflone
quinone methide
Tocopherols