Improved synthesis of (±)-linderol A and its first conversion to (±)-6-epi-adunctin E

Heterocycles

Volumn 65, Issue 5, 2005, Pages 1099-1109

  Yamashita, Masayuki ^a   Shimizu, Takashi ^a   Inaba, Tomoki ^a   Takada, Ai ^a   Takao, Ikuko ^a   Kawasaki, Ikuo ^a   Ohta, Shunsaku ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 31344432126     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-10345     Document Type: Article

References (21)

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8. Numbering according to that of linderol A (2) is used in a text.
9. 7. Decarboxylation of 6a under acidic condition afforded a complex mixture or low yield of 7. Attempts for alkaline hydrolysis of 6a resulted in almost complete recovery of 6a. The enolate anion generated first from the enol-ester (6a) would prevent approach of the hydroxy anion to the ester carbonyl group. Therefore, alkaline hydrolysis of the ethoxycarbonyl group in 6a was carried out after protection of the enol group.
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21. X-Ray crystallography of 11 analogue (A) was performed. The dihedral angle of (5a-H)-5a-6-(6-O) was -48 degrees, and that of (5a-H)-5a-6-(6-C) was 71 degrees. Crystallographic data (excluding structure factors) of A have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 260501. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk]. (Chemical Equation Presented).