메뉴 건너뛰기




Volumn 58, Issue 52, 2002, Pages 10353-10374

Studies directed toward the total synthesis of pinnatoxin A: Synthesis of the 6,5,6-dispiroketal (BCD ring) system by double hemiketal formation/hetero-Michael addition strategy

Author keywords

Dispiroketal; Hemiketal formation; Hetero Michael addition

Indexed keywords

ACETAL DERIVATIVE; LITHIUM DERIVATIVE; MARINE TOXIN; PINNATOXIN A; UNCLASSIFIED DRUG;

EID: 0037164607     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)01379-0     Document Type: Article
Times cited : (32)

References (66)
  • 24
    • 0035810406 scopus 로고    scopus 로고
    • Recent efforts toward the synthesis of azaspiracids, a novel class of marine toxins, have also raised the problem of stereocontrol in the construction of a dispiroketal fused to a tetrahydrofuran: (a) Dounay A.B., Forsyth C.J. Org. Lett. 3:2001;975-978 (b) Carter R.G., Graves D.E. Tetrahedron Lett. 42:2001;6035-6039 (c) Nicolaou K.C., Qian W., Bernal F., Uesaka N., Pihko P.M., Hinrichs J. Angew. Chem., Int. Ed. 40:2001;4068-4071.
    • (2001) Org. Lett. , vol.3 , pp. 975-978
    • Dounay, A.B.1    Forsyth, C.J.2
  • 25
    • 0035959520 scopus 로고    scopus 로고
    • Recent efforts toward the synthesis of azaspiracids, a novel class of marine toxins, have also raised the problem of stereocontrol in the construction of a dispiroketal fused to a tetrahydrofuran: (a) Dounay A.B., Forsyth C.J. Org. Lett. 3:2001;975-978 (b) Carter R.G., Graves D.E. Tetrahedron Lett. 42:2001;6035-6039 (c) Nicolaou K.C., Qian W., Bernal F., Uesaka N., Pihko P.M., Hinrichs J. Angew. Chem., Int. Ed. 40:2001;4068-4071.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6035-6039
    • Carter, R.G.1    Graves, D.E.2
  • 26
    • 0035813929 scopus 로고    scopus 로고
    • Recent efforts toward the synthesis of azaspiracids, a novel class of marine toxins, have also raised the problem of stereocontrol in the construction of a dispiroketal fused to a tetrahydrofuran: (a) Dounay A.B., Forsyth C.J. Org. Lett. 3:2001;975-978 (b) Carter R.G., Graves D.E. Tetrahedron Lett. 42:2001;6035-6039 (c) Nicolaou K.C., Qian W., Bernal F., Uesaka N., Pihko P.M., Hinrichs J. Angew. Chem., Int. Ed. 40:2001;4068-4071.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 4068-4071
    • Nicolaou, K.C.1    Qian, W.2    Bernal, F.3    Uesaka, N.4    Pihko, P.M.5    Hinrichs, J.6
  • 27
    • 33845185080 scopus 로고
    • For a review on the synthesis of spiroketals, see: Perron F., Albizati K.F. Chem. Rev. 89:1989;1617-1661.
    • (1989) Chem. Rev. , vol.89 , pp. 1617-1661
    • Perron, F.1    Albizati, K.F.2
  • 31
    • 0033580904 scopus 로고    scopus 로고
    • For a review on the synthesis of dispiroketals, see: Brimble M.A., Farès F.A. Tetrahedron. 55:1999;7661-7706.
    • (1999) Tetrahedron , vol.55 , pp. 7661-7706
    • Brimble, M.A.1    Farès, F.A.2
  • 43
    • 0021171455 scopus 로고
    • Masamune S., Ma P., Okumoto H., Ellingboe J.W., Ito Y. J. Org. Chem. 49:1984;2834-2837. (R)-Butane-1,2,4-triol can be obtained from D-malic acid in 69% yield over four steps: Mori K., Takigawa T., Matsuo T. Tetrahedron. 35:1979;933-940.
    • (1984) J. Org. Chem. , vol.49 , pp. 2834-2837
    • Masamune, S.1    Ma, P.2    Okumoto, H.3    Ellingboe, J.W.4    Ito, Y.5
  • 44
    • 0018429424 scopus 로고
    • Masamune S., Ma P., Okumoto H., Ellingboe J.W., Ito Y. J. Org. Chem. 49:1984;2834-2837. (R)-Butane-1,2,4-triol can be obtained from D-malic acid in 69% yield over four steps: Mori K., Takigawa T., Matsuo T. Tetrahedron. 35:1979;933-940.
    • (1979) Tetrahedron , vol.35 , pp. 933-940
    • Mori, K.1    Takigawa, T.2    Matsuo, T.3
  • 61
    • 0012007064 scopus 로고    scopus 로고
    • note
    • 2, nearly identical ratios of dispiroketal isomers 52-54 at equilibrium in favor of 53 were obtained, with no trace of the desired isomer 20. It was therefore concluded that the C23 configurations of 52-54 should be the same but opposite to that of 20.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.