Original scientific paper

A Transfer Alkylation Approach to Pentalenolactone

Barry M. Trost ; McElvain Laboratories of Organic Chemistry, Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706,U.S.A.
Lawrence S. Melvin, Jr. ; McElvain Laboratories of Organic Chemistry, Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706,U.S.A.

Abstract

Pentalenolactone, an antibiotic and antitumor agent which is a representative of the polycondensed cyclopentanoid natural products, requires the construction of a highly functionalized bicyclo[3.3.0]octyl system. Using the principle of transfer alkylation, a simple route to an acyclic precursor which involves anet y attack of a polyenolate allows the development of a [4+ 1] strategy to the basic ring system. Overall, an eight step route to an excellent precursor to pentalenolactone emerges. Using a further four step sequence, the fully elaborated ring system of pentalenolactone is created. In addition to the transfer alkylation strategy, a novel bromination utilizing liquid bromine as a solvent and a chemoselective unravelling of the resultant tribromide is reported.

Keywords

Hrčak ID:

178049

URI

https://hrcak.srce.hr/178049

Publication date:

6.3.1986.

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