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Volumn 132, Issue 14, 2010, Pages 5300-5308

Biomimetic syntheses from squalene-like precursors: Synthesis of ent- abudinol B and reassessment of the structure of muzitone

Author keywords

[No Author keywords available]

Indexed keywords

BIOMIMETIC SYNTHESIS; CYCLIZATIONS; FUNCTIONALIZED; MARINE NATURAL PRODUCTS; STEREOSELECTIVE SYNTHESIS; STRUCTURAL PATTERN;

EID: 77950852292     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1006806     Document Type: Article
Times cited : (28)

References (69)
  • 8
    • 0033597150 scopus 로고    scopus 로고
    • Note
    • Rudi, A., Yosief, T., Schleyer, M., and Kashman, Y. Tetrahedron 1999, 55, 5555 The stereochemistry of the C23 alcohol of abudinol B and corresponding C19 alcohol of muzitone is incorrectly shown as the R isomer in Figure 2 of ref 2a but correctly depicted with S stereochemistry in Scheme 1 (communication with Prof. Yoel Kashman).
    • (1999) Tetrahedron , vol.55 , pp. 5555
    • Rudi, A.1    Yosief, T.2    Schleyer, M.3    Kashman, Y.4
  • 30
    • 33745700292 scopus 로고    scopus 로고
    • Note
    • Given that d -epoxone (derived from d -fructose) was more easily prepared than l -epoxone, we intended from the outset to prepare the enantiomers of the natural products 2 and 5. Zhao, M.-X. and Shi, Y. J. Org. Chem. 2006, 71, 5377
    • (2006) J. Org. Chem. , vol.71 , pp. 5377
    • Zhao, M.-X.1    Shi, Y.2
  • 33
    • 30744447448 scopus 로고    scopus 로고
    • For selected papers, see:
    • Yoder, R. A. and Johnston, J. N. Chem. Rev. 2005, 105, 4730 For selected papers, see.
    • (2005) Chem. Rev. , vol.105 , pp. 4730
    • Yoder, R.A.1    Johnston, J.N.2
  • 56
    • 77950854555 scopus 로고    scopus 로고
    • Note
    • 4, resulted in lower yields of products or no reaction.
  • 63
    • 77950797416 scopus 로고    scopus 로고
    • Note
    • Other methylenation reagents attempted included the Tebbe reagent, Petasis reagent, and Julia tetrazole sulfone under various conditions.
  • 64
    • 77950841827 scopus 로고    scopus 로고
    • Note
    • A bicyclic compound bearing exo -methylene at C10 was also observed as a minor byproduct. However, this byproduct could not be purified and thus was not unambiguously characterized.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.