Total synthesis of highly oxygenated phomopsol B via acid-induced etherification to construct a bridged structure

The first total synthesis of phomopsol B has been achieved in a racemic form. The synthesis comprises a deacetylative cyclization to construct a bicyclic skeleton followed by primary alcohol-assisted dihydroxylation, ether cyclization to construct a dioxabicyclo [3.2.1] skeleton and gamma-lactone fo...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 60; no. 1; pp. 95 - 97
Main Authors Kawamoto, Yuichiro, Nishitani, Ayaka, Yoshimura, Yukari, Kobayashi, Toyoharu, Ito, Hisanaka
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 19.12.2023
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Oxidation
Physical Sciences
Science & Technology
Synthesis
SECONDARY ALCOHOLS
SELECTIVE OXIDATION
ALDEHYDES
CONVERSION
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Summary:The first total synthesis of phomopsol B has been achieved in a racemic form. The synthesis comprises a deacetylative cyclization to construct a bicyclic skeleton followed by primary alcohol-assisted dihydroxylation, ether cyclization to construct a dioxabicyclo [3.2.1] skeleton and gamma-lactone formation based on oxidation by TEMPO.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1359-7345
1364-548X
DOI:10.1039/d3cc05130g