Total Synthesis of Sarcophytonolide H and Isosarcophytonolide D: Structural Revision of Isosarcophytonolide D and Structure–Antifouling Activity Relationship of Sarcophytonolide H

The first total syntheses of sarcophytonolide H and the originally proposed and correct structures of isosarcophytonolide D have been achieved via transannular ring-closing metathesis (RCM). These total syntheses culminated in the stereostructural confirmation of sarcophytonolide H and the reassignm...

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Published inOrganic letters Vol. 18; no. 9; pp. 2110 - 2113
Main Authors Takamura, Hiroyoshi, Kikuchi, Takahiro, Endo, Noriyuki, Fukuda, Yuji, Kadota, Isao
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.05.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SECONDARY ALCOHOLS
SAMARIUM DIIODIDE
CHEMICAL-SYNTHESIS
ALDEHYDES
LATUM
ABSOLUTE-CONFIGURATIONS
SOFT
CEMBRANOLIDES
METATHESIS
MARINE NATURAL-PRODUCTS
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Summary:The first total syntheses of sarcophytonolide H and the originally proposed and correct structures of isosarcophytonolide D have been achieved via transannular ring-closing metathesis (RCM). These total syntheses culminated in the stereostructural confirmation of sarcophytonolide H and the reassignment of isosarcophytonolide D, respectively. The antifouling activity of the synthetic sarcophytonolide H and its analogues was also evaluated.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b00737