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Scientific article
English

Total synthesis of the macrolide (+)-aspicilin by an asymmetrically catalyzed macrocyclization of an ω-Alkynal ester

Published inTetrahedron letters, vol. 36, no. 15, p. 2607-2610
Publication date1995-04-10
First online date2000-06-14
Abstract

ω-Alkynal ester 3, prepared from (S)-propylene oxide 4, yields the macrocyclic (6R)-allylic alcohol 2 (60% yield, 83% d.e.) in one operation via monohydroboration, boron/zinc-transmetalation and (−)-DAIB “catalyzed” intramolecular alkenylzinc/aldehyde addition. Introduction of the C(2)–C(3) double bond by selenoxide elimination (2 → 8), hydroxy-directed epoxidation (8 → 9), acetate assisted α-epoxide opening (10 → 12) and acidic methanolysis provides pure (+)-aspicilin (1) in 22% overall yield from 4.

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Citation (ISO format)
VON OPPOLZER, Wolfgang, RADINOV, Rumen N., DE BRABANDER, Jef. Total synthesis of the macrolide (+)-aspicilin by an asymmetrically catalyzed macrocyclization of an ω-Alkynal ester. In: Tetrahedron letters, 1995, vol. 36, n° 15, p. 2607–2610. doi: 10.1016/0040-4039(95)00351-c
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ISSN of the journal0040-4039
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