Pyrrolizidine alkaloids by intramolecular palladium-catalysed allylic alkylation: Synthesis of (±)-isoretronecanol

DOI: 10.1002/ejoc.200400135

Source and publish data:

European Journal of Organic Chemistry p. 2840 - 2847 (2004)

Update date:2022-08-05

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Authors:

Lemaire, Sebastien

Giambastiani, Giuliano

Prestat, Guillaume

Poli, Giovanni

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Article abstract of DOI:10.1002/ejoc.200400135

An efficient and stereoconvergent approach to 3-substituted hexahydroindol-2-one derivatives by palladium-catalysed intramolecular allylic alkylation has been developed. Subsequently, the straightforward conversion of the hexahydroindol-2-one 7d into the alkaloid (±)-isoretronecanol has been performed. The synthesis entails 11 steps starting from 1,3-cyclohexadiene, affording the final target in a 29% overall yield. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Full text of DOI:10.1002/ejoc.200400135

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