Rapid biomimetic total synthesis of (±)-rossinone B

Ziyang Zhang; Jiahua Chen; Zhen Yang; Yefeng Tang

doi:10.1021/ol102438r

Rapid biomimetic total synthesis of (±)-rossinone B

Org Lett. 2010 Dec 3;12(23):5554-7. doi: 10.1021/ol102438r. Epub 2010 Nov 9.

Authors

Ziyang Zhang¹, Jiahua Chen, Zhen Yang, Yefeng Tang

Affiliation

¹ Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), College of Chemistry, Peking University, Beijing 100871, China.

PMID: 21062011
DOI: 10.1021/ol102438r

Abstract

A biomimetic total synthesis of (±)-rossinone B has been achieved through a highly efficient strategy featuring a series of rationally designed reactions, including a one-pot allylic rearrangement/oxidation reaction to generate the vinyl quinone 27, an intramolecular vinyl quinone Diels-Alder reaction to construct the linear 6-6-5 tricyclic core of 28, and a double conjugate addition/β-elimination cascade to complete the total synthesis of 1.

Publication types

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

MeSH terms

Biological Products / chemistry
Biomimetic Materials / chemical synthesis*
Molecular Structure
Terpenes / chemical synthesis*

Substances

Biological Products
Terpenes
rossinone B