Total Syntheses of Proposed Structures of 4,10-Dihydroxy-8,12-guaianolides

The first total syntheses of two 4,10-dihydroxy-8,12-guaianolides that were reported to be natural products were achieved. Toward the syntheses of a collection of related guaianolides, the typical 5,7-fused system of 8,12-guaianolides was constructed by a ring expansion reaction of a hydroxylated co...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 17; pp. 3297 - 3301
Main Authors Kimura, Yuki, Ohashi, Eisaku, Karanjit, Sangita, Taniguchi, Takashi, Nakayama, Atsushi, Imagawa, Hiroshi, Sato, Ryota, Namba, Kosuke
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.05.2022
Amer Chemical Soc
Subjects
Biological Products - chemistry
Chemistry
Chemistry, Organic
Molecular Structure
Physical Sciences
Science & Technology
CORONAFACIC ACID
GUAIANOLIDES
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Summary:The first total syntheses of two 4,10-dihydroxy-8,12-guaianolides that were reported to be natural products were achieved. Toward the syntheses of a collection of related guaianolides, the typical 5,7-fused system of 8,12-guaianolides was constructed by a ring expansion reaction of a hydroxylated coronafacic acid analogue that can be practically synthesized and optically resolved. The total syntheses of these compounds revealed that the previously reported structures of both natural products were incorrect.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01215