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Volumn 5, Issue 9, 2003, Pages 1447-1449

On the structure of passifloricin A: Asymmetric synthesis of the δ-lactones of (2Z,5S,7R,9S,11S)- and (2Z,5R,7R,9S,11S)-tetrahydroxyhexacos-2-enoic acid

Author keywords

[No Author keywords available]

Indexed keywords

ACID; LACTONE; LACTONE DERIVATIVE; NATURAL PRODUCT; PASSIFLORICIN A; POLYKETIDE; TETRAHYDROXYHEXACOS 2 ENOIC ACID; UNCLASSIFIED DRUG; MONOUNSATURATED FATTY ACID; PYRONE DERIVATIVE;

EID: 0042766867     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034182o     Document Type: Article
Times cited : (35)

References (33)
  • 12
    • 0027210757 scopus 로고
    • For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
    • (1993) J. Org. Chem. , vol.58 , pp. 1646-1648
    • Palomo, C.1    Aizpurua, J.M.2    Urchegi, R.3    García, J.M.4
  • 13
    • 0032871244 scopus 로고    scopus 로고
    • For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
    • (1999) Chem. Eur. J. , vol.5 , pp. 2850-2858
    • Schneider, C.1    Rehfeuter, M.2
  • 14
    • 0000575374 scopus 로고    scopus 로고
    • For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
    • (2000) Org. Lett. , vol.2 , pp. 1209-1212
    • Trieselmann, T.1    Hoffmann, R.W.2
  • 15
    • 0034609699 scopus 로고    scopus 로고
    • For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
    • (2000) Org. Lett. , vol.2 , pp. 3205-3208
    • Sarraf, S.T.1    Leighton, J.L.2
  • 16
    • 0035940146 scopus 로고    scopus 로고
    • See also ref 11b
    • For further, more recent methodologies toward 1,3-polyol segments, see, for example: (a) Palomo, C.; Aizpurua, J. M.; Urchegi, R.; García, J. M. J. Org. Chem. 1993, 58, 1646-1648. (b) Schneider, C.; Rehfeuter, M. Chem. Eur. J. 1999, 5, 2850-2858. (c) Trieselmann, T.; Hoffmann, R. W. Org. Lett. 2000, 2, 1209-1212. (d) Sarraf, S. T.; Leighton, J. L. Org. Lett. 2000, 2, 3205-3208. (e) Hunter, T. J.; O'Doherty, G. A. Org. Lett. 2001, 3, 2777-2780. See also ref 11b.
    • (2001) Org. Lett. , vol.3 , pp. 2777-2780
    • Hunter, T.J.1    O'Doherty, G.A.2
  • 19
    • 0141603174 scopus 로고    scopus 로고
    • note
    • Allylation under Keck and related conditions (ref 10) was unsuccessful here (extremely slow reaction). The use of the Duthaler-Hafner allylation reagent (ref 11) was discarded because of its very high price.
  • 24
    • 0141603173 scopus 로고    scopus 로고
    • note
    • Freshly prepared by PCC oxidation of n-hexadecanol.
  • 26
    • 0037000811 scopus 로고    scopus 로고
    • (b) For a recent review on asymmetric allylborations, see: Ramachandran, P. V. Aldrichimica Acta 2002, 35, 23-35.
    • (2002) Aldrichimica Acta , vol.35 , pp. 23-35
    • Ramachandran, P.V.1
  • 28
    • 0141714794 scopus 로고    scopus 로고
    • note
    • Chomatographic separation of diastereomers (6 + epimer) proved to be unfeasible. After desilylation, separation was possible and the pure diol 7 was then resitylated to 8.
  • 31
    • 0141491538 scopus 로고
    • Basic desilylation reagent TBAF gives rise to lactone-opening reactions in this type of compound: Nakata, T.; Hata, N.; Oishi, T. Heterocycles 1990, 30, 333-334.
    • (1990) Heterocycles , vol.30 , pp. 333-334
    • Nakata, T.1    Hata, N.2    Oishi, T.3
  • 32
    • 0141714793 scopus 로고    scopus 로고
    • note
    • 13C signals around 70 and 40 ppm.
  • 33
    • 0024347403 scopus 로고
    • (5S,7R,9R,11R)-Stereoisomer, found in another plant source, is also different from passifloricin A. Its structure has been confirmed by stereoselective synthesis: Nakata, T.; Suenaga, T.; Nakashima, K.; Oishi, T. Tetrahedron Lett. 1989, 30, 6529-6532.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 6529-6532
    • Nakata, T.1    Suenaga, T.2    Nakashima, K.3    Oishi, T.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.