Total Synthesis of (−)-Graminin A Based on Asymmetric Cyclization Carbonylation of Propargyl Acetate

The first total synthesis of (−)-graminin A is described. Key features of our synthetic approach involve a palladium-catalyzed asymmetric cyclization carbonylation of prochiral propargylic acetate, conversion of the orthoester product into methyl 4-oxo-3-furancarboxylate, and copper complex-mediated...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 84; no. 24; pp. 16268 - 16277
Main Authors Ito, Yoichi, Kusakabe, Taichi, Dhage, Yogesh Daulat, Takahashi, Keisuke, Sakata, Ken, Sasai, Hiroaki, Kato, Keisuke
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.12.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID
(+)-GREGATIN B
GRAMININ
C-H
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Summary:The first total synthesis of (−)-graminin A is described. Key features of our synthetic approach involve a palladium-catalyzed asymmetric cyclization carbonylation of prochiral propargylic acetate, conversion of the orthoester product into methyl 4-oxo-3-furancarboxylate, and copper complex-mediated aldol condensation of (+)-gregatin B bearing a diene moiety. A new synthesis of (+)-gregatin B and the first synthesis of (−)-graminin A were achieved.
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02886