Total synthesis of the Amaryllidaceae alkaloid clivonine.

Helmut Haning, Carles Giró-Mañas, Victoria L Paddock, Christian G Bochet, Andrew J P White, Gerald Bernardinelli, Inderjit Mann, Wolfang Oppolzer, Alan C Spivey

Bayer Schering Pharma AG, Müllerstr. 178, 13353, Berlin, Germany.

Organic & biomolecular chemistry 2011 Apr 21

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Two syntheses of the Amaryllidaceae alkaloid clivonine (1) are described. Both employ previously reported 7-arylhydrindane 6 as an intermediate but differ in the method employed for subsequent introduction of what becomes the ring-B lactone carbonyl carbon (C7). The synthesis featuring a Bischler-Napieralski reaction for this transformation constitutes the first asymmetric synthesis of natural (+)-clivonine. Crystal structures for compounds (±)-13, (±)-16, (-)-20 and (±)-28 are also reported.

Citation

Helmut Haning, Carles Giró-Mañas, Victoria L Paddock, Christian G Bochet, Andrew J P White, Gerald Bernardinelli, Inderjit Mann, Wolfang Oppolzer, Alan C Spivey. Total synthesis of the Amaryllidaceae alkaloid clivonine. Organic & biomolecular chemistry. 2011 Apr 21;9(8):2809-20