Total synthesis of the Amaryllidaceae alkaloid clivonine

Article Article scientifique Article Total synthesis of the Amaryllidaceae alkaloid clivonine eng 2011-03-02 2011-04-21 author Haning Helmut 93845 author Giró-Mañas Carles author Paddock Victoria L. author Bochet Christian 27518 author White Andrew J. P. author Bernardinelli Gérald Hugues 24765 author Mann Inderjit author Von Oppolzer Wolfgang 25270 author Spivey Alan Christopher 28370 2809-2820 10.1039/c0ob00895h 21365099 1477-0520 http://xlink.rsc.org/?DOI=c0ob00895h 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 lactonecarbonyl 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. Dewey 540 36 Département de chimie organique 141 false Organic & biomolecular chemistry 9 8 a183e61d-3039-4c1a-b105-cf587683148d Article (Published version) Restricted c0ob00895h(1).pdf 560545 application/pdf Vignette Public Get.gif 20097 image/gif restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Total synthesis of the Amaryllidaceae alkaloid clivonine	Organic & biomolecular chemistry			2011	119	0

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Haning, Helmut