Controlling benzylic functionality and stereochemistry: 1. Synthesis of the secopseudopterosin aglycone

McCombie, Stuart W, Cox, Brian, Lin, Sue-Ing, Ganguly, Ashit K and McPhail, Andrew T (1991) Controlling benzylic functionality and stereochemistry: 1. Synthesis of the secopseudopterosin aglycone. Tetrahedron Letters, 32 (19). pp. 2083-2086. ISSN 0040-4039

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Abstract

Directed, homogeneous hydrogenation of 1-(1-hydroxymethylethyl)-5-methoxy-3,4-dihydronaphthalene (7), followed by protection and selective benzylic oxidation gave the 1-oxo-(4R*, 11R*) compound (13). After addition of MeCeCl2, the natural C-1 stereochemistry was established by intramolecular hydride delivery from the di-t-butylsilylether. Final elaboration of the sidechain and the Ar ring substituents gave the secopseudopterosin aglycone other (3).

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Depositing User: Tom Gittoes
Date Deposited: 14 Jan 2015 10:27
Last Modified: 14 Jan 2015 10:27
URI: http://sro.sussex.ac.uk/id/eprint/52126
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