Enantioselective synthesis of (+)-decarestrictine L from (2E,5E)-dibenzyloxy-2,5-heptadien-4-ol

Authors
Esumi, T Kimura, R Mori, M Iwabuchi, Y Irie, H Hatakeyama, S
Citation
T. Esumi et al., Enantioselective synthesis of (+)-decarestrictine L from (2E,5E)-dibenzyloxy-2,5-heptadien-4-ol, HETEROCYCLE, 52(2), 2000, pp. 525-528
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
52
Issue
2
Year of publication
2000
Pages
525 - 528
Database
ISI
SICI code
0385-5414(20000201)52:2<525:ESO(LF>2.0.ZU;2-Z
Abstract
(+)-Decarestrictine L has been synthesized in enantiomerically pure form fr om (3R,4S)-1-benzyloxy-6-heptene-3,4-diol, prepared from (2E,5E)-1,7-dibenz yloxy-2,5-heptadien-4-ol, employing either Me2AlCl promoted methylative cle avage of (1R,5R,6S)-6-benzyloxy-2,9-dioxabicyclo[3.3.1]nonane or DIBAH prom oted reductive cleavage of (1R,5R,6S)-6-benzyloxy-1-methyl-2,9-dioxabicyclo [3.3.1]nonane for the construction of the substituted pyran ring system.