Enantioselective total syntheses of bengamides B and E

DOI: 10.1016/S0040-4039(00)79423-8

Source and publish data:

Tetrahedron Letters p. 5907 - 5910 (1991)

Update date:2022-08-05

Topics:

Authors:

Broka Broka

Ehrler Ehrler

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Article abstract of DOI:10.1016/S0040-4039(00)79423-8

Convergent total syntheses of two sponge-derived cyclolysine derivatives - bengamides B (1) and E (2) - have been accomplished. The polyhydroxylated side chain common to both natural products was obtained from L-glucose and the hydroxylated caprolactam moiety of 1 was prepared using Evans' oxazolidinone chemistry. In the course of this work a new Horner-Emmons reagent incorporating one of Evans' chiral auxiliaries was developed.

Full text of DOI:10.1016/S0040-4039(00)79423-8

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Product name:(E)-(2R,3S,4S,5R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide

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