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Volumn 126, Issue 20, 2004, Pages 6230-6231

A simple stereocontrolled synthesis of salinosporamide A

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; LACTACYSTIN BETA LACTONE; NATURAL PRODUCT; SALINOSPORAMIDE A; UNCLASSIFIED DRUG;

EID: 2442720189     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048613p     Document Type: Article
Times cited : (256)

References (19)
  • 17
    • 0032479233 scopus 로고    scopus 로고
    • The stereochemistry of the conversion 13 → 14, established by the identity of totally synthetic 1 with naturally formed salinosporamide A, is that predicted from a cyclic, chair-formed, six-membered transition state involving addition of the organozinc reagent to the sterically more accessible face of the formyl group. The use of 2-cyclohexenylzinc chloride is critical to successful formation of 14 because none of this product is obtained with 2-cyclohexenyllithium (probably because the initial carbonyl adduct undergoes retroaldol cleavage and decomposition; see: Corey, E. J.; Li, W.; Nagamitsu, T. Angew. Chem., Int. Ed. 1998, 37, 1676-1679).
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1676-1679
    • Corey, E.J.1    Li, W.2    Nagamitsu, T.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.