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On the structure of naturally-occurring (+)-methyl 3,4-anhydroshikimate

✍ Scribed by Harold B. Wood; Bruce Ganem

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 91 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93866-3

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✦ Synopsis

A two-step synthesis of enantiomericaily pure (+)-methyl 3,4-anhydroshikimate 2 from (-)-methyl shikimate 3 is described, leading to a revision in the properties reporfed for this natural product.

Recently two new metabolites 1 and 2 were isolated from the fungus Chalara microspora during a systematic search for medicinally active compounds. 1 The former, chaloxone, appears related to the epoxydon family 2 while the latter, methyl 3,4-anhydroshikimate, may be derived from shikimate-3-phosphate as an offshoot of the aromatic biosynthetic pathway in plants and microorganisms. 3 The structure of 2 was subsequently confirmed by a racemic muhistep synthesis and its absolute configuration reportedly established by partial resolution. 1

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