Synthesis of the AB Subunit of Angelmicin B Through a Tandem Alkoxy Radical Fragmentation-etherification Sequence

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2008 Mar 8

PMID 18324819

Citations 6

Authors

Jialiang Li

Louis J Todaro

David R Mootoo

Affiliations

Soon will be listed here.

Abstract

The synthesis of the tricyclic enone 2, corresponding to the AB subunit of the novel tyrosine kinase inhibitor angelmicin B, is described. The strategy centers on an intramolecular Diels-Alder (IMDA) reaction on triene 4 to provide the complex decalin 3, which is elaborated to 2. Other key steps are the formation of the THF ring in 2 through a tandem alkoxy radical fragmentation-etherification on the lactol derived from 3, and the synthesis of 4 via a ring-closing ene-yne metathesis (RCEYM).

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Synthesis of an A'B' Precursor to Angelmicin B: Product Diversification in the Suárez Lactol Fragmentation.

Li J, Todaro L, Mootoo D European J Org Chem. 2012; 2011(31):6281-6287.

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