A Total Synthesis of Galbonolide B

An ester enolate rearrangement/silicon mediated fragmentation cascade was used to convert 7 and 8 into the alcohol 9. The alcohol 9 was converted into the allylic alcohol 12 and then to the ester 14. A further ester enolate rearrangement furnished the stereochemical identity of galbonolide B 1. Base...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 72; no. 24; pp. 9387 - 9390
Main Authors Parsons, Philip J, Pennicott, Lewis, Eshelby, James, Goessman, Matthias, Highton, Adrian, Hitchcock, Peter
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.11.2007
Amer Chemical Soc
Subjects
Acetals - chemistry
Acetates - chemistry
Alkylation
Antifungal Agents - chemical synthesis
Chemistry
Chemistry, Organic
Cyclization
Exact sciences and technology
Lactones - chemical synthesis
Models, Chemical
Organic chemistry
Physical Sciences
Propanols - chemistry
Science & Technology
STEREOCHEMICAL CONTROL
ESTER ENOLATE
ENOLATE CLAISEN REARRANGEMENT
Chemical rearrangement
Acetic acid esters
Deprotection
Alcohol
Stereochemistry
Alkylation
Allylic compound
Total synthesis
Fragmentation
Acetal
Ester
Macrocyclization
Silicon
Enolate
Successive reaction
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Summary:An ester enolate rearrangement/silicon mediated fragmentation cascade was used to convert 7 and 8 into the alcohol 9. The alcohol 9 was converted into the allylic alcohol 12 and then to the ester 14. A further ester enolate rearrangement furnished the stereochemical identity of galbonolide B 1. Base mediated macrocyclization of the acetate ester 16 followed by base mediated alkylation and acetal deprotection gave galbonolide B 1.
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ark:/67375/TPS-VZS6DXWP-N
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo701509r