BRIEF DIELS ALDER SYNTHESIS OF (+/-)-METHYL 5-EPISHIKIMATE AND (+/-)-METHYL CIS-3,4-DIHYDRO-3,4-DIHYDROXYBENZOATE

DOI: 10.1016/S0040-4039(00)86246-2

Source and publish data:

Tetrahedron Letters p. 4745 - 4746 (1983)

Update date:2022-08-03

Topics:

Authors:

Campbell, Malcolm M.

Kaye, Aston D.

Sainsbury, Malcolm

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Article abstract of DOI:10.1016/S0040-4039(00)86246-2

Base-catalysed ring opening of the acetonide of cis-exo-2,3-dihydroxy-6-methoxycarbonyl-7-oxabicycloheptane affords a stereo-controlled route to (+/-)-methyl 5-epishikimate and thence, by an elimination process, to (+/-)-methyl-cis-3,4-dihydro-3,4-dihydroxybenzoate.

Full text of DOI:10.1016/S0040-4039(00)86246-2

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