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Issue 3, 2009
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Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18α-oleanane core and A-neo-18α-oleanene compounds from lupanes

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Abstract

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, 28,13β-lactonization occurred, without Wagner-Meerwein rearrangement. Under more vigorous reaction conditions, dehydration of the 3β-hydroxyl group and subsequent additional Wagner-Meerwein rearrangement led to the selective synthesis of A-neo-18α-oleanene compounds, in very high yields.

Graphical abstract: Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18α-oleanane core and A-neo-18α-oleanene compounds from lupanes

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Publication details

The article was received on 20 Aug 2008, accepted on 03 Nov 2008 and first published on 09 Dec 2008


Article type: Paper
DOI: 10.1039/B814448F
Citation: Org. Biomol. Chem., 2009,7, 508-517
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    Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18α-oleanane core and A-neo-18α-oleanene compounds from lupanes

    J. A. R. Salvador, R. M. A. Pinto, R. C. Santos, C. Le Roux, A. M. Beja and J. A. Paixão, Org. Biomol. Chem., 2009, 7, 508
    DOI: 10.1039/B814448F

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