LITHIATION OF BENZENE-DERIVATIVES PROMOTED BY BETA-FUNCTIONALIZED ALKYL-GROUPS - ASYMMETRIC-SYNTHESIS OF THE ISOCOUMARIN PORTION OF AI-77-B

Authors
BERTELLI L FIASCHI R NAPOLITANO E
Citation
L. Bertelli et al., LITHIATION OF BENZENE-DERIVATIVES PROMOTED BY BETA-FUNCTIONALIZED ALKYL-GROUPS - ASYMMETRIC-SYNTHESIS OF THE ISOCOUMARIN PORTION OF AI-77-B, Gazzetta chimica italiana, 123(12), 1993, pp. 669-672
Citations number
19
Categorie Soggetti
Chemistry
Journal title
Gazzetta chimica italiana → ACNP
ISSN journal
00165603
Volume
123
Issue
12
Year of publication
1993
Pages
669 - 672
Database
ISI
SICI code
0016-5603(1993)123:12<669:LOBPBB>2.0.ZU;2-W
Abstract
The title compound has been synthesised in five high-yielding steps fr om (2S,3R)-1,2-epoxy-5-methylhexan-1-ol, 12, prepared by Sharpless asy mmetric epoxidation of allylic alcohols. The key step of the sequence was the clean metallation at position 2' of the aromatic ring undergon e by enyl)-3-(1-methoxy-1-methylethoxy)-5-methylhexane, 14, which perm itted the introduction of the carboxyl group in that position and the construction of the isocoumarin ring.