STEREOCONTROLLED SYNTHESIS OF KEY INTERMEDIATES IN THE TOTAL SYNTHESIS OF ACETOGENINS OF ANNONACEAE

Authors
FIGADERE B CHABOCHE C PEYRAT JF CAVE A
Citation
B. Figadere et al., STEREOCONTROLLED SYNTHESIS OF KEY INTERMEDIATES IN THE TOTAL SYNTHESIS OF ACETOGENINS OF ANNONACEAE, Tetrahedron letters, 34(50), 1993, pp. 8093-8096
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
50
Year of publication
1993
Pages
8093 - 8096
Database
ISI
SICI code
0040-4039(1993)34:50<8093:SSOKII>2.0.ZU;2-D
Abstract
4S, 5S, 8S, 9S)- and (4R, 5S, 8S, 9S)-9-hydroxy-5,8-epoxy-henicosabuta nolides 3b and 4b, respectively, have been successfully synthesized fr om very inexpensive L-glutamic acid The key step of the synthetic sequ ence is an alkylation of lactol acetates 5a,b with 2-(trimethylsilylox y)-furan. Stereochemical relationship assignment of the obtained produ cts were deduced from NMR data, and by chemical correlation.