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A convergent total synthesis of (−)-anamarine from d-glucose

✍ Scribed by Frieder W Lichtenthaler; Klaus Lorenz; Wei-yong Ma

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
290 KB
Volume
28
Category
Article
ISSN
0040-4039

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✦ Synopsis

The di-acetonide of 6-deoxy-aLdehydo-D-qlucose Lz and (S,S)-2-ethoxy-6-triphenylphosphoniomethyl-dihydropyran iodide 2 are elaborated from D-glucose each in practicable procedures of 5 and 10 steps, resp., and subsequently joined to give, after oxidation, deprotection and acetylation, (-I-anamarine (en%:). The synthesis proves the absolute configuration of natural (+I-anamarine (2). A novel C,2 compound isolated in 1979 from the flowers and leaves of a Peruvian ~yptis species and named anamcrine2 was shown to have constitution 1 on the basis of 'H-, 13 C-NMR and X-ray crystal lographic data3, featuring R-configuration in the pyranoid ring and a rather unusual L-gluco arrangement in the C 6 -side chain.

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