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Volumn 13, Issue 12, 2011, Pages 3028-3031

Total synthesis of (-)-salinosporamide A

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; LACTONE; PROTEASOME; PYRROLE DERIVATIVE; SALINOSPORAMIDE A;

EID: 79958818188     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200886j     Document Type: Article
Times cited : (52)

References (36)
  • 25
    • 33846299580 scopus 로고    scopus 로고
    • For reviews of the syntheses, see:;, and ref 2f
    • For reviews of the syntheses, see: Shibasaki, M.; Kanai, M.; Fukuda, N. Chem.-Asian J. 2007, 2, 20 and ref 2f
    • (2007) Chem.-Asian J. , vol.2 , pp. 20
    • Shibasaki, M.1    Kanai, M.2    Fukuda, N.3
  • 26
    • 79958787314 scopus 로고    scopus 로고
    • In ref 4 the diastereoselective formation of a γ-lactam was reported as shown below. However, we could not apply this strategy to asymmetric synthesis because the reaction resulted in a complete racemization
    • In ref 4 the diastereoselective formation of a γ-lactam was reported as shown below. However, we could not apply this strategy to asymmetric synthesis because the reaction resulted in a complete racemization.
  • 32
    • 79958848835 scopus 로고    scopus 로고
    • The structure of 7a was determined by an X-ray crystallographic study
    • The structure of 7a was determined by an X-ray crystallographic study.
  • 33
    • 79958785186 scopus 로고    scopus 로고
    • 3OD (1:1)
    • 3OD (1:1).
  • 36
    • 79958839357 scopus 로고    scopus 로고
    • According to ref 3b, addition of the cyclohexenylzinc reagent gave poor selectivity when the lactam moiety was protected as its ethyl imidate. Thus protection of the nitrogen atom was essential to obtain the desired stereochemistry. We also tried introducing the cyclohexenyl moiety to the unprotected lactam by diastereoselective allylation followed by ring closing metathesis. In this case, the product turned out to be exclusively the undesired isomer
    • According to ref 3b, addition of the cyclohexenylzinc reagent gave poor selectivity when the lactam moiety was protected as its ethyl imidate. Thus protection of the nitrogen atom was essential to obtain the desired stereochemistry. We also tried introducing the cyclohexenyl moiety to the unprotected lactam by diastereoselective allylation followed by ring closing metathesis. In this case, the product turned out to be exclusively the undesired isomer.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.