Total synthesis of the Amaryllidaceae alkaloid clivonine.
نویسندگان
چکیده
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.
منابع مشابه
Total synthesis of the lycorenine-type amaryllidaceae alkaloid (+/-)-clivonine via a biomimetic ring-switch from a lycorine-type progenitor.
A fully diastereoselective total synthesis of the lycorenine-type Amaryllidaceae alkaloid (+/-)-clivonine (19) is reported via a route that employs for the first time a biomimetic ring-switch from a lycorine-type progenitor, thereby corroborating experimentally the biogenetic hypothesis first expounded for these compounds by Barton in 1960.
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 9 8 شماره
صفحات -
تاریخ انتشار 2011