Reactivity of (3-Methylpentadienyl)iron(1+) Cation: Late-stage Introduction of a (3-Methyl-2Z,4-pentadien-1-yl) Side Chain

Authors

  • Subhabrata Chaudhury
  • Shukun Li
  • William A. Donaldson Chemistry Department, Marquette University 2370 North 103rd Street P.O. Box 1881 , Milwaukee, WI 53201-1881 Wauwatosa, WI 53226 414-288-7374 FAX: 414-288-7066 414-475-0044

Abstract

The 3-methyl-2Z,4-pentadien-1-yl sidechain is found in various sesquiterpenes and diterpenes. A route for the late stage introduction of this functionality was developed which relies on nucleophilic attack on the (3-methylpentadienyl)iron(1+) cation, followed by oxidative decomplexation.  This methodology was applied to the synthesis of the proposed structure of heteroscyphic acid A methyl ester.  Realization of this synthesis led to a correction of the proposed structure.

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Published

2016-06-03

Issue

Vol. 5 No. 5 (2016)

Section

Organic Chemistry

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