A new asymmetric synthesis of the anti-tumor alkaloid (R)-(+)-Crispine A

Steven M. Allin; Sean N. Gaskell; Joannah M. R. Towler; Philip C. Bulman Page; Basu Saha; Michael J. McKenzie; William P. Martin

doi:10.1021/jo071235x

A new asymmetric synthesis of the anti-tumor alkaloid (R)-(+)-Crispine A

Steven M. Allin, Sean N. Gaskell, Joannah M. R. Towler, Philip C. Bulman Page, Basu Saha, Michael J. McKenzie, William P. Martin

Chemistry of Materials and Catalysis

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

73 Citations (Scopus)

Abstract

We report a novel, facile, and asymmetric approach for the synthesis of the anti-tumor alkaloid (+)-crispine A via a highly diastereoselective N-acyliminium cyclization reaction as a key synthetic step.

Original language	English
Pages (from-to)	8972-8975
Number of pages	4
Journal	The Journal of Organic Chemistry
Volume	72
Issue number	23
DOIs	https://doi.org/10.1021/jo071235x
Publication status	Published - 2007

Keywords

ACYLIMINIUM ION CYCLIZATION
(+/-)-CRISPINE-A
ALPHA-AMIDOALKYLATION REACTIONS
DERIVATIVES
ENANTIOMERS
PYRROLOISOQUINOLINE RING-SYSTEM
FACILE
STEREOSELECTIVE SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS

Access to Document

10.1021/jo071235x

Cite this

@article{ab38e5fa12bf40dfa51d39229bf085a9,

title = "A new asymmetric synthesis of the anti-tumor alkaloid (R)-(+)-Crispine A",

abstract = "We report a novel, facile, and asymmetric approach for the synthesis of the anti-tumor alkaloid (+)-crispine A via a highly diastereoselective N-acyliminium cyclization reaction as a key synthetic step.",

keywords = "ACYLIMINIUM ION CYCLIZATION, (+/-)-CRISPINE-A, ALPHA-AMIDOALKYLATION REACTIONS, DERIVATIVES, ENANTIOMERS, PYRROLOISOQUINOLINE RING-SYSTEM, FACILE, STEREOSELECTIVE SYNTHESIS, ENANTIOSELECTIVE SYNTHESIS",

author = "Allin, {Steven M.} and Gaskell, {Sean N.} and Towler, {Joannah M. R.} and {Bulman Page}, {Philip C.} and Basu Saha and McKenzie, {Michael J.} and Martin, {William P.}",

year = "2007",

doi = "10.1021/jo071235x",

language = "English",

volume = "72",

pages = "8972--8975",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "23",

}

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T1 - A new asymmetric synthesis of the anti-tumor alkaloid (R)-(+)-Crispine A

AU - Allin, Steven M.

AU - Gaskell, Sean N.

AU - Towler, Joannah M. R.

AU - Bulman Page, Philip C.

AU - Saha, Basu

AU - McKenzie, Michael J.

AU - Martin, William P.

PY - 2007

Y1 - 2007

N2 - We report a novel, facile, and asymmetric approach for the synthesis of the anti-tumor alkaloid (+)-crispine A via a highly diastereoselective N-acyliminium cyclization reaction as a key synthetic step.

AB - We report a novel, facile, and asymmetric approach for the synthesis of the anti-tumor alkaloid (+)-crispine A via a highly diastereoselective N-acyliminium cyclization reaction as a key synthetic step.

KW - ACYLIMINIUM ION CYCLIZATION

KW - (+/-)-CRISPINE-A

KW - ALPHA-AMIDOALKYLATION REACTIONS

KW - DERIVATIVES

KW - ENANTIOMERS

KW - PYRROLOISOQUINOLINE RING-SYSTEM

KW - FACILE

KW - STEREOSELECTIVE SYNTHESIS

KW - ENANTIOSELECTIVE SYNTHESIS

U2 - 10.1021/jo071235x

DO - 10.1021/jo071235x

M3 - Article

VL - 72

SP - 8972

EP - 8975

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -