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An enantioselective synthesis of the bicyclic core of the marine natural product awajanomycin

Pritchard, DR and Wilden, JD (2010) An enantioselective synthesis of the bicyclic core of the marine natural product awajanomycin. TETRAHEDRON LETT , 51 (14) 1819 - 1821. 10.1016/j.tetlet.2010.01.123.

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Abstract

A concise stereoselective synthesis of the N-benzylated bicyclic core of the marine natural product awajanomycin is described starting with naturally Occurring L-alanine. Key steps in the synthesis include a ring-closing metathesis to establish a delta-lactam ring followed by a stereoselective hydroxylation to instal the quaternary centre. (C) 2010 Elsevier Ltd. All rights reserved.

Type:Article
Title:An enantioselective synthesis of the bicyclic core of the marine natural product awajanomycin
DOI:10.1016/j.tetlet.2010.01.123
Keywords:Ring-closing metathesis, delta-Lactam, Acremonium sp., Diastereoselective hydroxylation, VINYL HALIDES, LACTONES, CARBONYLATION, DERIVATIVES, METATHESIS, ALCOHOLS, ROUTE
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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