10-Step Asymmetric Total Synthesis and Stereochemical Elucidation of (+)-DragmacidinD

The asymmetric synthesis of dragmacidinD (1) was completed in 10steps. Its sole stereocenter was set by using direct asymmetric alkylation enabled by a C2-symmetric tetramine and lithium N-(trimethylsilyl)-tert-butylamide as the enolization reagent. A central Larock indole synthesis was employed in...

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Published inAngewandte Chemie Vol. 127; no. 34; pp. 10109 - 10113
Main Authors Jackson, Jeffrey J, Kobayashi, Hiroyuki, Steffens, Sophia D, Zakarian, Armen
Format Journal Article
LanguageEnglish
German
Published Weinheim Wiley Subscription Services, Inc 17.08.2015
Subjects
Alkylation
Assembly
Asymmetry
Chemistry
Drag (hindrance)
Lithium
Natural products
Sole
Synthesis
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Summary:The asymmetric synthesis of dragmacidinD (1) was completed in 10steps. Its sole stereocenter was set by using direct asymmetric alkylation enabled by a C2-symmetric tetramine and lithium N-(trimethylsilyl)-tert-butylamide as the enolization reagent. A central Larock indole synthesis was employed in a convergent assembly of the heterocyclic subunits. The stereochemical evidence from this work strongly supports the predicted S configuration at the 6''' position, which is consistent with other members of the dragmacidin family of natural products.
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ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201504113