A chemoenzymatic total synthesis of the protoilludane aryl ester (+)-armillarivin

Brett D Schwartz; Eliška Matoušová; Richard White; Martin G Banwell; Anthony C Willis

doi:10.1021/ol400583c

A chemoenzymatic total synthesis of the protoilludane aryl ester (+)-armillarivin

Org Lett. 2013 Apr 19;15(8):1934-7. doi: 10.1021/ol400583c. Epub 2013 Apr 3.

Authors

Brett D Schwartz¹, Eliška Matoušová, Richard White, Martin G Banwell, Anthony C Willis

Affiliation

¹ Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200, Australia.

PMID: 23550589
DOI: 10.1021/ol400583c

Abstract

The title natural product, 1, has been synthesized in 20 steps from the enantiomerically pure cis-1,2-dihydrocatechol 2, itself obtained through the whole-cell biotransformation of toluene. The pivotal steps in the reaction sequence involve a Diels-Alder cycloaddition reaction between diene 2 and cyclopentenone (3) and the photochemically promoted 1,3-acyl rearrangement of the bicyclo[2.2.2]oct-4-en-1-one 20 derived from the cycloadduct 4.

Publication types

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

MeSH terms

Biological Products / chemical synthesis*
Biological Products / chemistry
Cyclopentanes / chemistry
Esters
Molecular Structure
Polycyclic Sesquiterpenes
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry
Stereoisomerism

Substances

Biological Products
Cyclopentanes
Esters
Polycyclic Sesquiterpenes
Sesquiterpenes
protoilludane
armillarivin
cyclopentenone