Document Detail


Carotenoids and related polyenes, part 12. First total synthesis and absolute configuration of 3'-deoxycapsanthin and 3,4-didehydroxy-3'-deoxycapsanthin.
MedLine Citation:
PMID:  20930405     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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).
Authors:
Yumiko Yamano; Mahankhali Venu Chary; Akimori Wada
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Chemical & pharmaceutical bulletin     Volume:  58     ISSN:  1347-5223     ISO Abbreviation:  Chem. Pharm. Bull.     Publication Date:  2010 Oct 
Date Detail:
Created Date:  2010-10-08     Completed Date:  2011-02-02     Revised Date:  2011-03-08    
Medline Journal Info:
Nlm Unique ID:  0377775     Medline TA:  Chem Pharm Bull (Tokyo)     Country:  Japan    
Other Details:
Languages:  eng     Pagination:  1362-5     Citation Subset:  IM    
Affiliation:
Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, Japan. y-yamano@kobepharma-u.ac.jp
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MeSH Terms
Descriptor/Qualifier:
Capsicum / chemistry
Carotenoids / chemical synthesis,  chemistry*
Magnetic Resonance Spectroscopy
Molecular Conformation
Polyenes / chemistry*
Chemical
Reg. No./Substance:
0/3'-deoxycapsanthin; 0/3,4-didehydroxy-3'-deoxycapsanthin; 0/Polyenes; 36-88-4/Carotenoids

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