Azomethine Ylide Cycloaddition/Reductive Heterocyclization Approach to Oxindole Alkaloids: Asymmetric Sinthesis of (-)-Horsfiline

G. CRAVOTTO; Giovanni Battista GIOVENZANA; T. PILATI; M. SISTI; G. PALMISANO

doi:10.1021/jo015854w

Azomethine Ylide Cycloaddition/Reductive Heterocyclization Approach to Oxindole Alkaloids: Asymmetric Sinthesis of (-)-Horsfiline

G. CRAVOTTO
, Giovanni Battista GIOVENZANA
, T. PILATI
, M. SISTI
, G. PALMISANO

Department of Pharmaceutical Sciences

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

Abstract

The intermolecular [3 + 2] annulation of azomethine ylides with 2(2-nitrophenyl)acrylate dienophiles followed by reductive heterocyclization affords the spiro(indole-pyrrolidine) ring system. Hence, this enable us to accomplish a concise and highly enantioselective synthesis of (−)-horsfiline 1, based on chiral auxiliary-directed π-face discrimination in the 1,3-dipolar cycloaddition of (1S,2R)-2-phenyl-1-cyclohexyl ester 4f with N-methylazomethine ylide.

Original language	English
Pages (from-to)	8447-8453
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	66
Issue number	25
DOIs	https://doi.org/10.1021/jo015854w
Publication status	Published - 2001

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http://hdl.handle.net/11579/7489

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title = "Azomethine Ylide Cycloaddition/Reductive Heterocyclization Approach to Oxindole Alkaloids: Asymmetric Sinthesis of (-)-Horsfiline",

abstract = "The intermolecular [3 + 2] annulation of azomethine ylides with 2(2-nitrophenyl)acrylate dienophiles followed by reductive heterocyclization affords the spiro(indole-pyrrolidine) ring system. Hence, this enable us to accomplish a concise and highly enantioselective synthesis of (−)-horsfiline 1, based on chiral auxiliary-directed π-face discrimination in the 1,3-dipolar cycloaddition of (1S,2R)-2-phenyl-1-cyclohexyl ester 4f with N-methylazomethine ylide.",

author = "G. CRAVOTTO and GIOVENZANA, \{Giovanni Battista\} and T. PILATI and M. SISTI and G. PALMISANO",

year = "2001",

doi = "10.1021/jo015854w",

language = "English",

volume = "66",

pages = "8447--8453",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - Azomethine Ylide Cycloaddition/Reductive Heterocyclization Approach to Oxindole Alkaloids: Asymmetric Sinthesis of (-)-Horsfiline

AU - CRAVOTTO, G.

AU - GIOVENZANA, Giovanni Battista

AU - PILATI, T.

AU - SISTI, M.

AU - PALMISANO, G.

PY - 2001

Y1 - 2001

N2 - The intermolecular [3 + 2] annulation of azomethine ylides with 2(2-nitrophenyl)acrylate dienophiles followed by reductive heterocyclization affords the spiro(indole-pyrrolidine) ring system. Hence, this enable us to accomplish a concise and highly enantioselective synthesis of (−)-horsfiline 1, based on chiral auxiliary-directed π-face discrimination in the 1,3-dipolar cycloaddition of (1S,2R)-2-phenyl-1-cyclohexyl ester 4f with N-methylazomethine ylide.

AB - The intermolecular [3 + 2] annulation of azomethine ylides with 2(2-nitrophenyl)acrylate dienophiles followed by reductive heterocyclization affords the spiro(indole-pyrrolidine) ring system. Hence, this enable us to accomplish a concise and highly enantioselective synthesis of (−)-horsfiline 1, based on chiral auxiliary-directed π-face discrimination in the 1,3-dipolar cycloaddition of (1S,2R)-2-phenyl-1-cyclohexyl ester 4f with N-methylazomethine ylide.

UR - https://iris.uniupo.it/handle/11579/7489

U2 - 10.1021/jo015854w

DO - 10.1021/jo015854w

M3 - Article

SN - 0022-3263

VL - 66

SP - 8447

EP - 8453

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

Azomethine Ylide Cycloaddition/Reductive Heterocyclization Approach to Oxindole Alkaloids: Asymmetric Sinthesis of (-)-Horsfiline

Abstract

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