Total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide, a new biologically active delta-lactone produced by Seiridium unicorne

Authors
Toshima, H Sato, H Ichihara, A
Citation
H. Toshima et al., Total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide, a new biologically active delta-lactone produced by Seiridium unicorne, TETRAHEDRON, 55(9), 1999, pp. 2581-2590
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
9
Year of publication
1999
Pages
2581 - 2590
Database
ISI
SICI code
0040-4020(19990226)55:9<2581:TSO(AN>2.0.ZU;2-K
Abstract
The first total synthesis of (2S,3R,5S)-(-)-2,3-dihydroxytetradecan-5-olide (1), a new biologically active delta-lactone produced by Seiridium unicome , was accomplished from (R)-malic acid In connection with the determination of the absolute configuration of 1, (2R,3S,5R)-(+)-2,3-dihydroxytetradecan -5-olide (ent-1) was also synthesized from D-glucose. (C) 1999 Elsevier Sci ence Ltd. All rights reserved.