Evolution of Dithiane-Based Strategies for the Construction of Architecturally Complex Natural Products

Umpolung-based strategies play a significant role in organic synthesis. Particularly important are 1,3-dithiane linchpins, which serve as convenient acyl anion equivalents. The general synthetic accessibility and impressive reactivity of 1,3-dithianes have thus led to widespread application. Since t...

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Bibliographic Details
Published inAccounts of chemical research Vol. 37; no. 6; pp. 365 - 377
Main Authors Smith, Amos B, Adams, Christopher M
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 01.06.2004
Subjects
Alkaloids - chemistry
Biological Products - chemistry
Indicators and Reagents
Proteins - chemistry
Quinolizines - chemistry
Sulfur Compounds - chemistry
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Summary:Umpolung-based strategies play a significant role in organic synthesis. Particularly important are 1,3-dithiane linchpins, which serve as convenient acyl anion equivalents. The general synthetic accessibility and impressive reactivity of 1,3-dithianes have thus led to widespread application. Since the late 1970s, dithianes have featured prominently in our program directed toward the synthesis of complex natural and unnatural products, both for effective union of advanced fragments and for multicomponent linchpin couplings. In this Account, we present the evolution of dithiane chemistry in our laboratory.
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ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0001-4842
1520-4898
DOI:10.1021/ar030245r