Synthetic studies of himbacine, a potent antagonist of the muscarinic M2 subtype receptor 1. Stereoselective total synthesis and antagonistic activity of enantiomeric pairs of himbacine and (2′S,6′R)-diepihimbacine, 4-epihimbacine, and novel himbacine congeners

Tetrahedron

Volumn 58, Issue 50, 2002, Pages 9903-9923

  Takadoi, Masanori ^a   Katoh, Tadashi ^b   Ishiwata, Akihiro ^b   Terashima, Shiro ^b  

^a KYORIN PHARMACEUTICAL CO LTD   (Japan)

^b SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

Alkaloids; Asymmetric synthesis; Diels Alder reactions; Natural products

Indexed keywords

4 EPIHIMBACINE; DIEPIHIMBACINE; FURAN DERIVATIVE; HIMBACINE; MUSCARINIC M2 RECEPTOR; MUSCARINIC RECEPTOR BLOCKING AGENT; TETRAHYDROISOBENZOFURAN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DIELS ALDER REACTION; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

BETULACEAE;

EID: 0037049284     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01358-3     Document Type: Article

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64. The crystallographic data (excluding structure factors) for structures 6, 4a, 4b, 14a reported in this paper have been deposited to the Cambridge Crystallographic Data Centre (CCDC) as supplementary publication numbers CCDC 183422, 183423, 183424, and 183425, respectively. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: +44-1223-336033; e-mail: deposit@ccdc.cam.ac.uk).