Nature knows best: An amazing reaction cascade is uncovered by design and discovery

被引:150
作者
Heathcock, CH
机构
[1] Department of Chemistry, University of California, Berkeley
关键词
D O I
10.1073/pnas.93.25.14323
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
The Daphniphyllum alkaloids are a group of highly complex polycyclic alkaloids, Examination of the structures if several members of this family of natural products led to a hypothesis about their mode of biosynthesis (depicted in Scheme I), Based on this hypothetical biosynthetic pathway, a laboratory synthesis was designed that incorporated as a key transformation the novel one-pot transformation of dialdehyde 24 to pentacyclic unsaturated amine 25, This process turned out to be an exceptionally efficient way to construct the pentacyclic nucleus of the Daphniphyllum alkaloids, However, a purely fortuitous discovery, resulting from accidental use of methylamine rather than ammonia, led to a great improvement in the synthesis and suggests an even more attractive possible biosynthesis.
引用
收藏
页码:14323 / 14327
页数:5
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