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Tetracyclic triterpenes. Part 2. A synthetic approach to cucurbitacins
Authors:
- Zdzisław Paryzek
Abstract
Efficient 19(10 → 9β) methyl migration leading to compounds with the cucurbitane skeleton occurs when 3β-acetoxy-9β,11β- epoxylanostan-7-one (1) is treated with boron trifluoride-diethyl ether in acetic anhydride. The major product (2) has the double bond in the 5,6-position which is common for natural cucurbitacins. The factors influencing the direction of the rearrangement are discussed. Several transformations including the removal of the 7-carbonyl group and epimerization of C-10 are described.
- Record ID
- UAM9422cb2c9dd342d89dfc1a4863925c38
- Author
- Journal series
- Journal of the Chemical Society, Perkin Transactions 1, ISSN 1470-4358
- Issue year
- 1979
- Pages
- 1222-1227
- ASJC Classification
- Language
- (en) English
- Score (nominal)
- 0
- Score source
- journalList
- Publication indicators
- = 14
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- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAM9422cb2c9dd342d89dfc1a4863925c38/
- URN
urn:amu-prod:UAM9422cb2c9dd342d89dfc1a4863925c38
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