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

Research output: Contribution to journalArticle

61 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3999-4002
Number of pages4
JournalOrganic Letters
Volume8
Issue number18
DOIs
StatePublished - Aug 31 2006
Externally publishedYes

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Succinic Anhydrides
Lactams
alkaloids
Imines
Cycloaddition
Anhydrides
Cycloaddition Reaction
cycloaddition
anhydrides
Alkaloids
imines
Anions
Carbon
selectivity
anions
acids
carbon
synthesis
martinellic acid
martinelline

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Cycloaddition reactions of imines with 3-thiosuccinic anhydrides : Synthesis of the tricyclic core of martinellic acid. / Ng, Pui Yee; Masse, Craig E.; Shaw, Jared T.

In: Organic Letters, Vol. 8, No. 18, 31.08.2006, p. 3999-4002.

Research output: Contribution to journalArticle

Ng, Pui Yee ; Masse, Craig E. ; Shaw, Jared T. / Cycloaddition reactions of imines with 3-thiosuccinic anhydrides : Synthesis of the tricyclic core of martinellic acid. In: Organic Letters. 2006 ; Vol. 8, No. 18. pp. 3999-4002.
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