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Volumn 3, Issue 5, 2001, Pages 675-678

Stereoselective synthesis of substituted γ-butyrolactones by the [3 + 2] annulation of allylic silanes with chlorosulfonyl isocyanate: Enantioselective total synthesis of (+)-blastmycinone

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; ANTIINFECTIVE AGENT; BLASTOMYCINONE; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; ISOCYANIC ACID DERIVATIVE; SILANE DERIVATIVE;

EID: 0035826331     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0069960     Document Type: Article
Times cited : (67)

References (39)
  • 3
    • 0034625935 scopus 로고    scopus 로고
    • For selected recent examples, see: (a) Zhung, Q.; Lu, X. J. Am. Chem. Soc. 2000, 122, 7604-7605.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7604-7605
    • Zhung, Q.1    Lu, X.2
  • 21
    • 0041405376 scopus 로고    scopus 로고
    • note
    • 2. Temperature did not greatly affect the C=O to C=N annulation ratio.
  • 22
    • 0041906504 scopus 로고    scopus 로고
    • note
    • Only the C=N annulation product lactam 4b was obtained if the annulation reaction was conducted in toluene, see ref 6.
  • 23
    • 0041405375 scopus 로고    scopus 로고
    • note
    • A control experiment showed that no interconversion occurred between iminolactone 3a and N-chlorosulfonyl lactam 4a.
  • 32
    • 0010640653 scopus 로고
    • The enantiomeric excess of 12 was determined by GC analysis of its Mosher ester: Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543-2549.
    • (1969) J. Org. Chem. , vol.34 , pp. 2543-2549
    • Dale, J.A.1    Dull, D.L.2    Mosher, H.S.3
  • 35
    • 0042908546 scopus 로고    scopus 로고
    • note
    • The enantiomeric excess of 14 and 15 was determined by HPLC analysis using a Chiracel OD-H column, and the enantiomencally enriched material was compared with racemic material.
  • 39
    • 0000365479 scopus 로고    scopus 로고
    • 2NCO in the formal synthesis of a lactam natural product, see: Roberson, C. W.; Woerpel, K. A. Org. Lett. 2000, 2, 621-623.
    • (2000) Org. Lett. , vol.2 , pp. 621-623
    • Roberson, C.W.1    Woerpel, K.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.