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Volumn 39, Issue 6, 2000, Pages 1125-1128

Synthesis of the (9S,18R) diastereomer of cyclamenol A

Author keywords

Chemical biology; Leukocyte adhesion; Medicinal chemistry; Natural products; Total synthesis

Indexed keywords

CYCLAMENOL A; LACTAM DERIVATIVE; POLYENE ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

EID: 0034677846     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000317)39:6<1125::AID-ANIE1125>3.0.CO;2-O     Document Type: Article
Times cited : (47)

References (47)
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    • A search of the Beilstein CrossFire database for related substructures revealed pronounced preference for these configurations in other natural products.
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    • 1. Thus, the 12,13-cis isomer is energetically much more favored than the corresponding trans isomer, and the formation of the trans isomer can be ruled out for energetic reasons. In addition, for related tetraene and polyene systems it is known that the energetically less favorable isomers spontaneously isomerize to the more stable analogues: a) K. C. Nicolaou, S. E. Webber, J. Ramphal, Y. Abe, Angrew. Chem. 1987, 99, 1077-1079; Angew. Chem. Int. Ed. Engl. 1987, 26, 1019-1021;
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    • 1H NMR spectrum of the O-silylated thionocarbonate obtained from diol 18 displays a coupling constant of 7 Hz for the two CH(OCS) signals of the five-membered ring. This indicates that the two hydrogen atoms are cis-oriented (in related compounds coupling constants of 6.5-7.8 Hz are found;
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    • note
    • We are grateful to Dr. B. Fugmann, Bayer AG, for samples of natural cyclamenol A.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.