Faculté des sciences

Total synthesis of the Amaryllidaceae alkaloid clivonine

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

In: Organic & Biomolecular Chemistry, 2011, vol. 9, p. 2809-2820

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... Plus

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    Summary
    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.