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Volumn 39, Issue 21, 1998, Pages 3359-3362

"Symmetry" in the synthesis of the A-ring of a vitamin D hybrid analogue with significant transactivation activity: A combinatorial sequence of regioselective propiolate-ene, catalytic enantioselective epoxidation and carbonyl-ene cyclization reactions

Author keywords

[No Author keywords available]

Indexed keywords

VITAMIN D DERIVATIVE;

EID: 0032555010     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00272-X     Document Type: Article
Times cited : (39)

References (53)
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    • Ph. D. dissertation, Tokyo Institute of Technology, Dec.
    • (a) Shimizu, M. Ph. D. dissertation, Tokyo Institute of Technology, Dec. 1993.
    • (1993)
    • Shimizu, M.1
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    • (b) Regioselective carbonyl-ene reactions with allylic and homoallylic alcohols: Mikami, K.; Shimizu, M.; Nakai, T. J. Org. Chem. 1991, 56, 2952-2953.
    • (1991) J. Org. Chem. , vol.56 , pp. 2952-2953
    • Mikami, K.1    Shimizu, M.2    Nakai, T.3
  • 17
  • 22
    • 0001290261 scopus 로고
    • Trost, B. M.; Fleming, I., Eds.; Pergamon: London
    • (b) Snider, B. B. in "Comprehensive Organic Synthesis"; Trost, B. M.; Fleming, I., Eds.; Pergamon: London, 1991; Vol. 2, pp. 527-561
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 527-561
    • Snider, B.B.1
  • 26
    • 85034159065 scopus 로고    scopus 로고
    • MPM: p-methoxyphenylmethyl
    • MPM: p-methoxyphenylmethyl.
  • 27
    • 0002350886 scopus 로고
    • Symmetry in syntheses: Reviews: Ward, R. S.; Chem. Soc. Rev. 1990, 19, 1-19;
    • (1990) Chem. Soc. Rev. , vol.19 , pp. 1-19
    • Ward, R.S.1
  • 42
    • 0026344849 scopus 로고
    • For asymmetric (2,4) and (3,4) ene cyclizations catalyzed by binaphthol-derived titanium complex, see: Mikami, K.; Sawa, E.; Terada, M. Tetrahedron Asymm. 1991, 2, 1403-1412.
    • (1991) Tetrahedron Asymm. , vol.2 , pp. 1403-1412
    • Mikami, K.1    Sawa, E.2    Terada, M.3
  • 43
    • 85034179428 scopus 로고    scopus 로고
    • note
    • 3).
  • 45
    • 0001197645 scopus 로고
    • For STO-3G and 3-21G calculations on 5-membered transition states (ref. 9d) of thermal ene reactions, see: Loncharich, R. J.; Houk, K. N. J. Am. Chem. Soc. 1987, 109, 6947-6952.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 6947-6952
    • Loncharich, R.J.1    Houk, K.N.2
  • 46
    • 0001533172 scopus 로고
    • For axial vs. equatorial orientation of carbonyl group in ene cyclization reactions, see: Maruoka, K.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1990, 112, 9011-9012;
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 9011-9012
    • Maruoka, K.1    Ooi, T.2    Yamamoto, H.3
  • 48
    • 0000087777 scopus 로고
    • However, they proposed an equatorial arrangement of carbonyl group complexed with sterically bulky MABR leading to 1,3-cis-cyclohexanol. Also see: Marshall, J. A.; Anderson, M. W. J. Org. Chem. 1992, 57, 5851-5856.
    • (1992) J. Org. Chem. , vol.57 , pp. 5851-5856
    • Marshall, J.A.1    Anderson, M.W.2
  • 50
  • 52
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    • For cyclic allylic strain concept, see: Johnson, F. Chem. Rev. 1968, 68, 375-413.
    • (1968) Chem. Rev. , vol.68 , pp. 375-413
    • Johnson, F.1
  • 53
    • 85034165289 scopus 로고    scopus 로고
    • note
    • Sterically bulky tert-butyldiphenylsilyl protective group instead of benzyl group leads to the four possible isomers (trans, Z), (trans, E), (cis, Z), and (cis, E) in a ratio of 48 : 40 : 8 : 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.