Study on fungitoxic 3-amino-2-piperidinone-containing lipids: Revised structure of cepaciamide A and structural determination of its closely related lipid, cepaciamide B

Authors
Toshima, H Maru, K Jiao, Y Yoshihara, T Ichihara, A
Citation
H. Toshima et al., Study on fungitoxic 3-amino-2-piperidinone-containing lipids: Revised structure of cepaciamide A and structural determination of its closely related lipid, cepaciamide B, TETRAHEDR L, 40(5), 1999, pp. 935-938
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
5
Year of publication
1999
Pages
935 - 938
Database
ISI
SICI code
0040-4039(19990129)40:5<935:SOF3LR>2.0.ZU;2-2
Abstract
The structure of cepaciamide A was revised to be (3R,3'S,2"S,11"S,12"R)-3-[ 3'-(2"-hydroxy-11", 12"-methyleneoctadecanoyloxy)hexadecamido]-2-piperidino ne with respect to the absolute configuration of the C-3'- and C-2"-positio ns and the position of the cyclopropane ring by using synthetic methods. Th e structure of cepaciamide B was also determined to be (3R,3'S,2"S,11"Z)-3- [3'-(2"-hydroxy-11"-octadecenoyloxy)hexadecamido]-2-piperidinone. (C) 1999 Elsevier Science Ltd. All rights reserved.