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Volumn 62, Issue 15, 1997, Pages 5023-5033

Applications of organosulfur chemistry to organic synthesis: Total synthesis of (+)-himbeline and (+)-himbacine

Author keywords

[No Author keywords available]

Indexed keywords

HIMBACINE; HIMBELINE; SULFONE; UNCLASSIFIED DRUG;

EID: 0030757959     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970612a     Document Type: Article
Times cited : (61)

References (51)
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    • 9 It belongs to the Magnoliales order and thus is somewhat related to magnolias. We thank Professor Frank R. Stermitz of Colorado State University for bringing this error to our attention.
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    • note
    • The appearance of a small signal at about δ 6.79 in the cycloadditions of 19a and 19b suggested that a small amount of third stereoisomer was formed in these cycloaddition reactions. This signal did not appear in the Lewis acid promoted reactions.
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    • note
    • We thank Dr. Judith Gallucci of the Department of Chemistry Crystallography Facility for determining the crystal structures of 21, 31, and 35.
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    • note
    • 3, 75 MHz) δ 22.0 (q), 26.0 (t), 26.3 (t), 31.1 (t), 31.9 (t), 33.5 (t), 39.8 (d), 41.0 (d), 42.1 (d), 46.9 (d), 48.6 (d), 76.7 (d), 116.7 (t), 139.7 (d), 178.1 (s)]. This material could have resulted from sequential carbonyl addition, alcohol acylation, a Grob fragmentation, and vinyl sulfone reduction. (Matrix Presented)
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    • The preparation of sulfone 35 followed the same general path used to prepare sulfone 30 (see Experimental Section), only (S)-2-(hydroxymethyl)pyrrolidine was used as the starting material (Jing Li, unpublished results).
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    • note
    • 9
  • 47
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    • note
    • 2 Spectral data were also in accord with the assigned structure.
  • 50
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    • note
    • We thank Professor Viresh Rawal for kindly providing a sample of the natural product.
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    • note
    • The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.