| Carotenoids and related polyenes, part 12. First total synthesis and absolute configuration of 3'-deoxycapsanthin and 3,4-didehydroxy-3'-deoxycapsanthin. | |
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MedLine Citation:
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PMID: 20930405 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The synthesis of 3'-deoxycapsanthin (1) and 3,4-didehydroxy-3'-deoxycapsanthin (2), carotenoids of paprika, has been achieved by employing Lewis acid-promoted regio- and stereoselective rearrangement of the C(15)-epoxy dienal 5a. The absolute stereochemistry of the newly formed C-5 chiral center of rearrangement product 6a was determined to be (R) from its alternative synthesis derived from (+)-(R)-camphonanic acid (11). |
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Authors:
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Yumiko Yamano; Mahankhali Venu Chary; Akimori Wada |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Chemical & pharmaceutical bulletin Volume: 58 ISSN: 1347-5223 ISO Abbreviation: Chem. Pharm. Bull. Publication Date: 2010 Oct |
Date Detail:
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Created Date: 2010-10-08 Completed Date: 2011-02-02 Revised Date: 2011-03-08 |
Medline Journal Info:
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Nlm Unique ID: 0377775 Medline TA: Chem Pharm Bull (Tokyo) Country: Japan |
Other Details:
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Languages: eng Pagination: 1362-5 Citation Subset: IM |
Affiliation:
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Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, Japan. y-yamano@kobepharma-u.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Capsicum
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chemistry Carotenoids / chemical synthesis, chemistry* Magnetic Resonance Spectroscopy Molecular Conformation Polyenes / chemistry* |
| Chemical | |
Reg. No./Substance:
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0/3'-deoxycapsanthin; 0/3,4-didehydroxy-3'-deoxycapsanthin; 0/Polyenes; 36-88-4/Carotenoids |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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