Total Synthesis of Gymnocin‑A

A convergent total synthesis of cytotoxic marine natural polycyclic ether, gymnocin-A (1), is described. The synthesis features three iterations of an oxiranyl anion strategy, involving base-mediated cycloetherification, ring expansion, and reductive etherification, for the construction of the FGH f...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 137; no. 45; pp. 14513 - 14516
Main Authors Sakai, Takeo, Matsushita, Shingo, Arakawa, Shogo, Mori, Koichi, Tanimoto, Miki, Tokumasu, Akihiro, Yoshida, Tatsuji, Mori, Yuji
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.11.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Ethers, Cyclic - chemical synthesis
Ethers, Cyclic - chemistry
Molecular Conformation
Physical Sciences
Science & Technology
Stereoisomerism
ORGANIC-SYNTHESIS
RING EXPANSION
GYMNODINIUM-MIKIMOTOI
POLYETHER
FUSED POLYCYCLIC ETHERS
RED TIDE DINOFLAGELLATE
STEREOSELECTIVE-SYNTHESIS
BETA-ALKOXYACRYLATES
MARINE TOXINS
CONVERGENT STRATEGIES
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Summary:A convergent total synthesis of cytotoxic marine natural polycyclic ether, gymnocin-A (1), is described. The synthesis features three iterations of an oxiranyl anion strategy, involving base-mediated cycloetherification, ring expansion, and reductive etherification, for the construction of the FGH fragment and for its coupling with the ABC and KLMN fragments.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b10082