共 19 条
Nature knows best: An amazing reaction cascade is uncovered by design and discovery
被引:150
作者:

Heathcock, CH
论文数: 0 引用数: 0
h-index: 0
机构: Department of Chemistry, University of California, Berkeley
机构:
[1] Department of Chemistry, University of California, Berkeley
来源:
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.
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页码:14323 / 14327
页数:5
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