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Total synthesis of the β-amyrin derivatives olean-13(18)-ene and 18α-olean-12-ene

✍ Scribed by E. Ghera; F. Sondheimer

Publisher
Elsevier Science
Year
1964
Tongue
French
Weight
177 KB
Volume
5
Category
Article
ISSN
0040-4039

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✦ Synopsis

We report the total synthesis of the racemlc /l -amyrin derivatives olean-13(18)-ene (XII) and l&r-olesn-12-ene (XIII) by a direct route, not involving relays. Trevious syntheses of fl -amyrin derivatives using natural materials as relays have been described4.

Condensation of the Grignard derivative of the acetylenic carbinol I5 with the cis-decalone II6 yielded an isomeric mixture of acetylenic 1,4-dials, which -

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The 13C NMR spectra of some pentacyclic triterpenoids, 3~-acetoxy-ll-oxo-olean-12-ene-30-oic acid methyl ester, 3~-acetoxy-ll-oxo-olean-12-ene-29-oic acid methyl ester, the corresponding 11-desoxo methyl esters, 3~-acetoxy-ll-oxo-18cw-olean-l2-en-30-oic acid methyl ester and 3~-acetoxy-ll-oxo-18~-ol