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Volumn 51, Issue 32, 2010, Pages 4263-4266

Studies toward the total synthesis of armatol F: Stereoselective construction of the C6 and C7 stereocenters and formation of the A-ring skeleton

Author keywords

[No Author keywords available]

Indexed keywords

ARMATOL F; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77955309819     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.026     Document Type: Article
Times cited : (6)

References (46)
  • 2
    • 0001418722 scopus 로고
    • Examples of natural r-2-alkyl-t-3-hydroxy-c-3-methyloxepanes. Hemibrevetoxin B: A.V.K. Prasad, and Y. Shimizu J. Am. Chem. Soc. 111 1989 6476
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6476
    • Prasad, A.V.K.1    Shimizu, Y.2
  • 7
  • 14
    • 0000268652 scopus 로고
    • We expect the formation of intermediate Z-ketene silyl acetal 5 in the Ireland-Claisen rearrangement of 6 from the stereochemistry of product 4 obtained. The selective formation of Z-ketene silyl acetal intermediates in the Claisen rearrangement reactions of allyl glycolate ester derivatives has been expected from the stereochemistry of the major products by several research groups, see: see also Ref. 17: T. Sato, K. Tajima, and T. Fujisawa Tetrahedron Lett. 24 1983 729
    • (1983) Tetrahedron Lett. , vol.24 , pp. 729
    • Sato, T.1    Tajima, K.2    Fujisawa, T.3
  • 32
    • 77955304689 scopus 로고    scopus 로고
    • note
    • The configuration of the newly forming stereocenter (C4) of 7 was confirmed by NMR analysis of a single diastereomeric 5-hydroxy-4-{2-(4- methoxyphenoxy)propyl}-2-phenyl-1,3-dioxane obtained through a process including conventional hydrogenation of 7, separation of epimers at C6, hydrolysis of the acetonide, and benzylidene acetal formation.
  • 34
    • 77955305159 scopus 로고    scopus 로고
    • note
    • 5 The reduced coordination ability of the α-oxygen of ent-6 due to steric hindrance may interfere with the Z-enolate formation to result in the low ratio of ent-4 to 17 in polar solvents. However, in toluene, the low solvation ability of toluene may destabilize the E-enolate rather than the Z-enolate, stabilized by the cyclic chelate, to enhance the ratio of ent-4.
  • 37
    • 77955303533 scopus 로고    scopus 로고
    • The time-dependent increase of the ratio of ent-4 might be attributable to the different lifetimes of E- and Z-enolates
    • The time-dependent increase of the ratio of ent-4 might be attributable to the different lifetimes of E- and Z-enolates.
  • 44
    • 77955308555 scopus 로고    scopus 로고
    • note
    • +]: 292.1674, found: 292.1668.
  • 46
    • 77955303632 scopus 로고    scopus 로고
    • The details will be described elsewhere
    • The details will be described elsewhere.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.