Highly Stereocontrolled Synyhesis of Some Trioxygenated Cyclohexenes: An Asymmetric Total Synthesis of (-)-Methyl Triacetyl-4-epishikimate

DOI: 10.1021/ja00283a036

Source and publish data:

Journal of the American Chemical Society p. 7373 - 7377 (1986)

Update date:2022-09-26

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Authors:

Posner, Gary H.

Wettlaufer, David G.

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Article abstract of DOI:10.1021/ja00283a036

Polyfunctional bicyclic lactone (-)-1 serves as a chiron for preparation of 3,4,6-trioxygenated cyclohexene (-)-5a in 56.6percent overall yield and for synthesis of (-)-methyl triacetyl-4-epishikimate, (-)-12, in 14 steps and in 23.4percent overall yield.

Full text of DOI:10.1021/ja00283a036

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Product name:(3aR,7R,7aR)-2,2-Dimethyl-7-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester

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