期刊
ORGANIC & BIOMOLECULAR CHEMISTRY
卷 7, 期 3, 页码 508-517出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b814448f
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资金
- Universidade de Coimbra [SFRH/BD/18013/2004]
- Fundacao para a Ciencia e Tecnologia [SFRH/BD/23770/2005]
The use of bismuth(III) salts as catalysts for the Wagner-Meerwein rearrangement of lupane derivatives with expansion of ring E and formation of an additional O-containing ring is reported. This process has also been extended to other terpenes, such as the sesquiterpene (-)-caryophyllene oxide. When the reaction was performed with oleanonic acid, 28,13 beta-lactonization occurred, without Wagner-Meerwein rearrangement. Under more vigorous reaction conditions, dehydration of the 3 beta-hydroxyl group and subsequent additional Wagner-Meerwein rearrangement led to the selective synthesis of A-neo-18 alpha-oleanene compounds, in very high yields.
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