Total synthesis and adjuvant activity of all stereoisomers of pinellic acid

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 5, 2003, Pages 937-941

  Shirahata, Tatsuya ^a   Sunazuka, Toshiaki ^a   Yoshida, Kiminari ^a   Yamamoto, Daisuke ^a   Harigaya, Yoshihiko ^a   Nagai, Takayuki ^a   Kiyohara, Hiroaki ^a   Yamada, Haruki ^a   Kuwajima, Isao ^a   Omura, Satoshi ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; INFLUENZA VACCINE; PINNELIC ACID; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; DIHYDROXYLATION; DRUG ACTIVITY; DRUG SYNTHESIS; INFLUENZA; ISOMER; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; VACCINATION;

EID: 0037430536     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)01069-7     Document Type: Article

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8. 3) afforded 3:2 mixture of 9,12-anti, and 9, 12-syn-triol, because of the steric hindrance of 12-OTIPS. The reduction of (+)-8 by (S)-BINAL gave the lower diastereoselectivity; 13:1 (mis-matched), however, by (R)-BINAL gave the higher diastereoselectivity; >20:1 (matched).