Approach to cis-Phlegmarine Alkaloids via Stereodivergent Reduction: Total Synthesis of (+)-Serratezomine E and Putative Structure of (-)-Huperzine N

被引：24

作者：

Bosch, Caroline ^{[1
]}

Fiser, Bela ^{[2
]}

Gomez-Bengoa, Enrique ^{[2
]}

Bradshaw, Ben ^{[1
]}

Bonjoch, Josep ^{[1
]}

机构：

[1] Univ Barcelona, IBUB, Fac Farm, Lab Quim Organ, E-08028 Barcelona, Spain

[2] Univ Basque Country, Dept Quim Organ 1, San Sebastian 20018, Spain

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 20期

关键词：

LYCOPODIUM ALKALOIDS; ASYMMETRIC-SYNTHESIS; LYCOPOSERRAMINE-Z; NATURAL-PRODUCTS; HYDROGENATION;

D O I：

10.1021/acs.orglett.5b02581

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A unified strategy for the synthesis of the cis-phlegmarine group of alkaloids is presented, leading to the first synthesis of serratezomine E (1) as well as the putative structure of huperzine N (2). A contrasteric hydrogenation method was developed based on the use of Wilkinson's catalyst, which allowed the facial selectivity of standard hydrogenation to be completely overturned. Calculations were performed to determine the mechanism, and structures for huperzines M and N are reassigned.

引用

页码：5084 / 5087

页数：4

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