ABSOLUTE-CONFIGURATION OF METHYL 9E)-3,6-EPOXY-4,6,8-TRIETHYL-2,4,9-DODECATRIENOATE FROM THE SPONGE PLAKORTIS HALICHONDRIOIDES

Authors
SCHMIDT EW FAULKNER DJ
Citation
Ew. Schmidt et Dj. Faulkner, ABSOLUTE-CONFIGURATION OF METHYL 9E)-3,6-EPOXY-4,6,8-TRIETHYL-2,4,9-DODECATRIENOATE FROM THE SPONGE PLAKORTIS HALICHONDRIOIDES, Tetrahedron letters, 37(37), 1996, pp. 6681-6684
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
37
Year of publication
1996
Pages
6681 - 6684
Database
ISI
SICI code
0040-4039(1996)37:37<6681:AOM9>2.0.ZU;2-D
Abstract
The absolute stereochemistry of methyl ester 2, which is a major metab olite of the Caribbean sponge Plakortis halichondrioides, was determin ed to be 6R,8R by means of chemical degradation and application of a m odification of Mosher's method. The absolute configuration at C-8 was determined by analysis of the H-1 NMR spectra of the amides formed fro m the acid 4 and (R)- and (S)-phenylglycine methyl ester. Copyright (C ) 1996 Elsevier Science Ltd