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Volumn 118, Issue 24, 1996, Pages 5620-5633

A unified strategy for the stereocontrolled construction of structurally unusual sesquiterpene lactones. Asymmetric synthesis of vulgarolide and deoxocrispolide

Author keywords

[No Author keywords available]

Indexed keywords

DEOXOCRISPOLIDE; SESQUITERPENE LACTONE; UNCLASSIFIED DRUG; VULGAROLIDE;

EID: 0030054543     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960334h     Document Type: Article
Times cited : (22)

References (45)
  • 18
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    • Bromide 11 was prepared by hydrobromination of 3-buyyn-1-ol [Cousseau, J. Synthesis 1980, 805] followed by MOM protection of the hydroxyl substituent.
    • (1980) Synthesis , pp. 805
    • Cousseau, J.1
  • 24
    • 0028305025 scopus 로고
    • and earlier references cited therein
    • (f) Doyon, J.; He, W.; Paquette, L. A. J. Org. Chem. 1994, 59, 2033 and earlier references cited therein.
    • (1994) J. Org. Chem. , vol.59 , pp. 2033
    • Doyon, J.1    He, W.2    Paquette, L.A.3
  • 27
    • 8944220657 scopus 로고
    • The explosive nature of MoOPD caused us to abandon the use of this reagent. Consult Chem. Eng. News 1992, 70 (No. 37), p 2.
    • (1992) Chem. Eng. News , vol.70 , Issue.37 , pp. 2
  • 34
    • 8944225434 scopus 로고    scopus 로고
    • note
    • Strictly speaking, the structural features of 24 are insufficient to distinguish between the actual operation of a chair or boat transition state. The point is therefore a mute one. However, the normal energetic ordering of the two geometric options favors the chairlike option.
  • 38
    • 8944236026 scopus 로고    scopus 로고
    • note
    • We thank Professor W. C. Still (Columbia University) for making his program available for use and Prof. K. Steliou (Boston University) for providing us with updates of this software package.
  • 40
    • 8944226052 scopus 로고
    • Ph.D. Dissertation, The Ohio State University, Columbus, OH
    • Wang, X. Ph.D. Dissertation, The Ohio State University, Columbus, OH, 1994.
    • (1994)
    • Wang, X.1
  • 44
    • 0000010296 scopus 로고
    • Burgess, E. M.; Penton, H. R.; Taylor, E. A. J. Am. Chem. Soc. 1970, 92, 5224; J. Org. Chem. 1973, 38, 26.
    • (1973) J. Org. Chem. , vol.38 , pp. 26
  • 45
    • 0028912170 scopus 로고
    • The general experimental protocols followed in this study parallel those described in a recent report: Raquette, L. A.; Ezquerra, J.; He, W. J. Org. Chem. 1995, 60, 1435.
    • (1995) J. Org. Chem. , vol.60 , pp. 1435
    • Raquette, L.A.1    Ezquerra, J.2    He, W.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.