Efficient syntheses of crispine A and harmicine by Rh-catalyzed cyclohydrocarbonylation

Wen Hua Chiou; Gau Hong Lin; Che Cheng Hsu; Stephen J. Chaterpaul; Iwao Ojima

doi:10.1021/ol900702t

Efficient syntheses of crispine A and harmicine by Rh-catalyzed cyclohydrocarbonylation

Wen Hua Chiou
, Gau Hong Lin
, Che Cheng Hsu
, Stephen J. Chaterpaul
, Iwao Ojima

Chemistry

Stony Brook University

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

71 Scopus citations

Abstract

The first examples of Rh-catalyzed cyclohydrocarbonylation-bicyclization of N-allylic amides of arylacetic acids are reported. This novel carbonylative bicyclization process was successfully applied to the rapid syntheses of crispine A and its analogues (tricyclic indolizidine alkaloids) as well as harmicine (tetracyclic β-carboline alkaloid).

Original language	English
Pages (from-to)	2659-2662
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	12
DOIs	https://doi.org/10.1021/ol900702t
State	Published - Jun 18 2009

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title = "Efficient syntheses of crispine A and harmicine by Rh-catalyzed cyclohydrocarbonylation",

abstract = "The first examples of Rh-catalyzed cyclohydrocarbonylation-bicyclization of N-allylic amides of arylacetic acids are reported. This novel carbonylative bicyclization process was successfully applied to the rapid syntheses of crispine A and its analogues (tricyclic indolizidine alkaloids) as well as harmicine (tetracyclic β-carboline alkaloid).",

author = "Chiou, \{Wen Hua\} and Lin, \{Gau Hong\} and Hsu, \{Che Cheng\} and Chaterpaul, \{Stephen J.\} and Iwao Ojima",

year = "2009",

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doi = "10.1021/ol900702t",

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journal = "Organic Letters",

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T1 - Efficient syntheses of crispine A and harmicine by Rh-catalyzed cyclohydrocarbonylation

AU - Chiou, Wen Hua

AU - Lin, Gau Hong

AU - Hsu, Che Cheng

AU - Chaterpaul, Stephen J.

AU - Ojima, Iwao

PY - 2009/6/18

Y1 - 2009/6/18

N2 - The first examples of Rh-catalyzed cyclohydrocarbonylation-bicyclization of N-allylic amides of arylacetic acids are reported. This novel carbonylative bicyclization process was successfully applied to the rapid syntheses of crispine A and its analogues (tricyclic indolizidine alkaloids) as well as harmicine (tetracyclic β-carboline alkaloid).

AB - The first examples of Rh-catalyzed cyclohydrocarbonylation-bicyclization of N-allylic amides of arylacetic acids are reported. This novel carbonylative bicyclization process was successfully applied to the rapid syntheses of crispine A and its analogues (tricyclic indolizidine alkaloids) as well as harmicine (tetracyclic β-carboline alkaloid).

UR - https://www.scopus.com/pages/publications/67149089291

U2 - 10.1021/ol900702t

DO - 10.1021/ol900702t

M3 - Article

SN - 1523-7060

VL - 11

SP - 2659

EP - 2662

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Efficient syntheses of crispine A and harmicine by Rh-catalyzed cyclohydrocarbonylation

Abstract

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