Total Synthesis of a Diacetonide Derivative of Thuggacin A

A highly stereoselective total synthesis of the diacetonide derivative of the antibiotic thuggacin A has been described. The synthesis features the stereoselective Stille cross-coupling reaction to set up the whole carbon framework, aldol condensation to construct the highly substituted conjugated d...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 81; no. 5; pp. 1786 - 1797
Main Authors Yadav, Jhillu S, Dutta, Palash
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.03.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Lactones - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
KETONES
ANTIBIOTICS
STEREOSELECTIVE TOTAL-SYNTHESIS
REDUCTION
EFFICIENT
ESTERS
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Summary:A highly stereoselective total synthesis of the diacetonide derivative of the antibiotic thuggacin A has been described. The synthesis features the stereoselective Stille cross-coupling reaction to set up the whole carbon framework, aldol condensation to construct the highly substituted conjugated diene, non-Evans syn aldol, CBS reduction, Hantzsch’s thiazole synthesis, Horner–Wadsworth–Emmons reaction, and Shiina’s macrolactonization.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02426