Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: Synthesis of the tricyclic core of martinellic acid

Pui Yee Ng; Craig E. Masse; Jared T. Shaw

doi:10.1021/ol061473z

Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: Synthesis of the tricyclic core of martinellic acid

Pui Yee Ng, Craig E. Masse, Jared T. Shaw

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64 Scopus citations

Abstract

Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.

Original language	English (US)
Pages (from-to)	3999-4002
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	18
DOIs	https://doi.org/10.1021/ol061473z
State	Published - Aug 31 2006
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

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10.1021/ol061473z

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abstract = "Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.",

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AU - Masse, Craig E.

AU - Shaw, Jared T.

PY - 2006/8/31

Y1 - 2006/8/31

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AB - Arylthio-substituted succinic anhydrides undergo cycloaddition reactions with imines to produce γ-lactams in high yield and with high diastereoselectivity. The origin of the selectivity is proposed to result from anion-π repulsion in the transition state. The utility of this technique is demonstrated in a synthesis of the carbon framework common to the alkaloids martinellic acid and martinelline in five steps.

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Cycloaddition reactions of imines with 3-thiosuccinic anhydrides: Synthesis of the tricyclic core of martinellic acid

Abstract

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