Toward the synthesis of phomoidride D

Graham K Murphy; Tatsuya Shirahata; Naoto Hama; Aaron Bedermann; Ping Dong; Travis C McMahon; Barry M Twenter; David A Spiegel; Ivar M McDonald; Nobuaki Taniguchi; Munenori Inoue; John L Wood

doi:10.1021/jo302353g

Toward the synthesis of phomoidride D

J Org Chem. 2013 Jan 18;78(2):477-89. doi: 10.1021/jo302353g. Epub 2013 Jan 10.

Authors

Graham K Murphy¹, Tatsuya Shirahata, Naoto Hama, Aaron Bedermann, Ping Dong, Travis C McMahon, Barry M Twenter, David A Spiegel, Ivar M McDonald, Nobuaki Taniguchi, Munenori Inoue, John L Wood

Affiliation

¹ Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.

PMID: 23245580
DOI: 10.1021/jo302353g

Abstract

An efficient and highly stereoselective approach toward the phomoidride family of natural products is described. The carbocyclic core structure was assembled using a tandem phenolic oxidation/Diels-Alder cycloaddition and a tandem 5-exo-trig/5-exo-trig radical cyclization to deliver an isotwistane intermediate that, upon a late-stage xanthate-initiated Grob fragmentation, furnishes the requisite bicyclo[4.3.1]decene.

Publication types

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

MeSH terms

Alkenes / chemistry*
Biological Products / chemical synthesis*
Biological Products / chemistry*
Bridged Bicyclo Compounds / chemical synthesis*
Bridged Bicyclo Compounds / chemistry*
Cyclization
Maleic Anhydrides / chemical synthesis*
Maleic Anhydrides / chemistry*
Molecular Structure
Oxidation-Reduction
Stereoisomerism

Substances

Alkenes
Biological Products
Bridged Bicyclo Compounds
Maleic Anhydrides
phomoidride D