Tetrahedron Letters p. 8093 - 8096 (1993)
Update date:2022-07-29
Topics:
Figadere, Bruno
Chaboche, Christophe
Peyrat, Jean-Francois
Cave, Andre
(4S, 5S, 8S, 9S)- and (4R, 5S, 8S, 9S)-9-hydroxy-5,8-epoxy-henicosabutanolides 3b and 4b, respectively, have been successfully synthesized from very inexpensive L-glutamic acid. The key step of the synthetic sequence is an alkylation of lactol acetates 5a,b with 2-(trimethylsilyloxy)-furan. Stereochemical relationship assignment of the obtained products were deduced from NMR data, and by chemical correlation.
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