A synthetic approach to 3-hydroxy 4-substituted carboxylic acids based on the stereoselective reduction of 1-trimethyisilyl-1-alkyn-3-ones

Authors
Alemany, C Bach, J Garcia, J Lopez, M Rodriguez, AB
Citation
C. Alemany et al., A synthetic approach to 3-hydroxy 4-substituted carboxylic acids based on the stereoselective reduction of 1-trimethyisilyl-1-alkyn-3-ones, TETRAHEDRON, 56(47), 2000, pp. 9305-9312
Citations number
59
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
47
Year of publication
2000
Pages
9305 - 9312
Database
ISI
SICI code
0040-4020(20001117)56:47<9305:ASAT34>2.0.ZU;2-M
Abstract
The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethyl silyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydrox y 4-substituted carboxylic acids, common substructures of a number of biolo gically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constitu ents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.