Enantioselective syntheses of the alkaloids cis -195A (pumiliotoxin C) and trans -195A based on multiple applications of asymmetric catalysis

Martin Gärtner; Jianping Qu; Günter Helmchen

doi:10.1021/jo202241b

Enantioselective syntheses of the alkaloids cis -195A (pumiliotoxin C) and trans -195A based on multiple applications of asymmetric catalysis

Martin Gärtner, Jianping Qu, Günter Helmchen

Heidelberg University

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

Short enantio- and diastereoselective syntheses of the decahydroquinoline alkaloids cis- (pumiliotoxin C) and trans-195A are presented. Key steps are an enantioselective iridium-catalyzed allylic amination, a Suzuki-Miyaura coupling, a catalyst-controlled copper-catalyzed 1,4-addition, and a reductive amination.

Original language	English
Pages (from-to)	1186-1190
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	77
Issue number	2
DOIs	https://doi.org/10.1021/jo202241b
State	Published - 20 Jan 2012
Externally published	Yes

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abstract = "Short enantio- and diastereoselective syntheses of the decahydroquinoline alkaloids cis- (pumiliotoxin C) and trans-195A are presented. Key steps are an enantioselective iridium-catalyzed allylic amination, a Suzuki-Miyaura coupling, a catalyst-controlled copper-catalyzed 1,4-addition, and a reductive amination.",

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AU - Qu, Jianping

AU - Helmchen, Günter

PY - 2012/1/20

Y1 - 2012/1/20

N2 - Short enantio- and diastereoselective syntheses of the decahydroquinoline alkaloids cis- (pumiliotoxin C) and trans-195A are presented. Key steps are an enantioselective iridium-catalyzed allylic amination, a Suzuki-Miyaura coupling, a catalyst-controlled copper-catalyzed 1,4-addition, and a reductive amination.

AB - Short enantio- and diastereoselective syntheses of the decahydroquinoline alkaloids cis- (pumiliotoxin C) and trans-195A are presented. Key steps are an enantioselective iridium-catalyzed allylic amination, a Suzuki-Miyaura coupling, a catalyst-controlled copper-catalyzed 1,4-addition, and a reductive amination.

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ER -

Enantioselective syntheses of the alkaloids cis -195A (pumiliotoxin C) and trans -195A based on multiple applications of asymmetric catalysis

Abstract

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