메뉴 건너뛰기




Volumn 7, Issue 8, 2005, Pages 1477-1480

First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol

Author keywords

[No Author keywords available]

Indexed keywords

15 OXOPUUPEHENOL; ANTINEOPLASTIC AGENT; PALLADIUM; PHENOL DERIVATIVE; SCLAREOL; UNCLASSIFIED DRUG;

EID: 17844402678     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047332j     Document Type: Article
Times cited : (58)

References (46)
  • 1
    • 77957087867 scopus 로고
    • Atta-ur-Rahman, Ed; Elsevier Science: New York
    • (a) Capon, R. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed; Elsevier Science: New York, 1995; Vol. 15, pp 289-326.
    • (1995) Studies in Natural Products Chemistry , vol.15 , pp. 289-326
    • Capon, R.J.1
  • 14
    • 0003763664 scopus 로고    scopus 로고
    • and references therein
    • (e) Faulkner, D. J. Nat. Prod. Rep. 1998, 113-158 and references therein,
    • (1998) Nat. Prod. Rep. , pp. 113-158
    • Faulkner, D.J.1
  • 24
    • 0017880251 scopus 로고
    • Synthesis of 1a,b in racemic form: (a) Trammel, G. L. Tetrahedron Lett. 1978, 1525-1528. Synthesis of 1a in optically active form: (b) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. (c) Quideau, S.; Lebon, M.; Lamidey, A.-M. Org. Lett. 2002, 22, 3975-3978.
    • (1978) Tetrahedron Lett. , pp. 1525-1528
    • Trammel, G.L.1
  • 25
    • 0031592604 scopus 로고    scopus 로고
    • Synthesis of 1a,b in racemic form: (a) Trammel, G. L. Tetrahedron Lett. 1978, 1525-1528. Synthesis of 1a in optically active form: (b) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. (c) Quideau, S.; Lebon, M.; Lamidey, A.-M. Org. Lett. 2002, 22, 3975-3978.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 2325-2328
    • Barrero, A.F.1    Alvarez-Manzaneda, E.J.2    Chahboun, R.3
  • 26
    • 0037665998 scopus 로고    scopus 로고
    • Synthesis of 1a,b in racemic form: (a) Trammel, G. L. Tetrahedron Lett. 1978, 1525-1528. Synthesis of 1a in optically active form: (b) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R. Tetrahedron Lett. 1997, 38, 2325-2328. (c) Quideau, S.; Lebon, M.; Lamidey, A.-M. Org. Lett. 2002, 22, 3975-3978.
    • (2002) Org. Lett. , vol.22 , pp. 3975-3978
    • Quideau, S.1    Lebon, M.2    Lamidey, A.-M.3
  • 27
    • 0033601441 scopus 로고    scopus 로고
    • Synthesis of 2a,b in optically active form: (a) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208. Synthesis of 2b in optically active form: (b) Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391. (c) Armstrong, V.; Barrero, A. F.; Alvarez-Manzaneda, E. J.; Cortés, M.; Sepúlveda, B. J. Nat. Prod. 2003, 66, 1382-1383. (d) Ishibashi, H.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 11122-11123.
    • (1999) Tetrahedron , vol.55 , pp. 15181-15208
    • Barrero, A.F.1    Alvarez-Manzaneda, E.J.2    Chahboun, R.3    Cortés, M.4    Armstrong, V.5
  • 28
    • 0035906053 scopus 로고    scopus 로고
    • Synthesis of 2a,b in optically active form: (a) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208. Synthesis of 2b in optically active form: (b) Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391. (c) Armstrong, V.; Barrero, A. F.; Alvarez-Manzaneda, E. J.; Cortés, M.; Sepúlveda, B. J. Nat. Prod. 2003, 66, 1382-1383. (d) Ishibashi, H.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 11122-11123.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2389-2391
    • Maiti, S.1    Sengupta, S.2    Giri, C.3    Achari, B.4    Banerjee, A.K.5
  • 29
    • 0142187800 scopus 로고    scopus 로고
    • Synthesis of 2a,b in optically active form: (a) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208. Synthesis of 2b in optically active form: (b) Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391. (c) Armstrong, V.; Barrero, A. F.; Alvarez-Manzaneda, E. J.; Cortés, M.; Sepúlveda, B. J. Nat. Prod. 2003, 66, 1382-1383. (d) Ishibashi, H.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 11122-11123.
    • (2003) J. Nat. Prod. , vol.66 , pp. 1382-1383
    • Armstrong, V.1    Barrero, A.F.2    Alvarez-Manzaneda, E.J.3    Cortés, M.4    Sepúlveda, B.5
  • 30
    • 4544340203 scopus 로고    scopus 로고
    • Synthesis of 2a,b in optically active form: (a) Barrero, A. F.; Alvarez-Manzaneda, E. J.; Chahboun, R.; Cortés, M.; Armstrong, V. Tetrahedron 1999, 55, 15181-15208. Synthesis of 2b in optically active form: (b) Maiti, S.; Sengupta, S.; Giri, C.; Achari, B.; Banerjee, A. K. Tetrahedron Lett. 2001, 42, 2389-2391. (c) Armstrong, V.; Barrero, A. F.; Alvarez-Manzaneda, E. J.; Cortés, M.; Sepúlveda, B. J. Nat. Prod. 2003, 66, 1382-1383. (d) Ishibashi, H.; Ishihara, K.; Yamamoto, H. J. Am. Chem. Soc. 2004, 126, 11122-11123.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 11122-11123
    • Ishibashi, H.1    Ishihara, K.2    Yamamoto, H.3
  • 35
    • 0027953196 scopus 로고
    • - -Drimenol (14) can be obtained in optically pure form from trans,trans-farnesol. Resolution of racemic 14 was achieved via chromatographic separation of the diasteromeric camphonates. See ref 11 and (a) Jordine, C.; Bick, S.; Möller, U.; Welzel, P.; Daucher, B.; Maas, C. Tetrahedron 1994, 50, 139-160. (-)-Drimenol (14) can also be obtained from (-)-sclareol through drimenyl acetate in a five-step synthesis with 42% overall yield. See: (b) Barrero, A. F.; Alvarez-Manzaneda, E. J.: Altarejos, J.; Salido, S.; Ramos, J. M. Tetrahedron Lett. 1994, 35, 2945-2948. (c) Barrero, A. F.; Manzaneda, E. A.; Altarejos, J.; Salido, S.; Ramos, J. M.; Simmonds, M. J. S.; Blaney, W. M. Tetrahedron 1995, 51, 7435-7450.
    • (1994) Tetrahedron , vol.50 , pp. 139-160
    • Jordine, C.1    Bick, S.2    Möller, U.3    Welzel, P.4    Daucher, B.5    Maas, C.6
  • 36
    • 0028308760 scopus 로고
    • - -Drimenol (14) can be obtained in optically pure form from trans,trans-farnesol. Resolution of racemic 14 was achieved via chromatographic separation of the diasteromeric camphonates. See ref 11 and (a) Jordine, C.; Bick, S.; Möller, U.; Welzel, P.; Daucher, B.; Maas, C. Tetrahedron 1994, 50, 139-160. (-)-Drimenol (14) can also be obtained from (-)-sclareol through drimenyl acetate in a five-step synthesis with 42% overall yield. See: (b) Barrero, A. F.; Alvarez-Manzaneda, E. J.: Altarejos, J.; Salido, S.; Ramos, J. M. Tetrahedron Lett. 1994, 35, 2945-2948. (c) Barrero, A. F.; Manzaneda, E. A.; Altarejos, J.; Salido, S.; Ramos, J. M.; Simmonds, M. J. S.; Blaney, W. M. Tetrahedron 1995, 51, 7435-7450.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 2945-2948
    • Barrero, A.F.1    Alvarez-Manzaneda, E.J.2    Altarejos, J.3    Salido, S.4    Ramos, J.M.5
  • 37
    • 0029017762 scopus 로고
    • - -Drimenol (14) can be obtained in optically pure form from trans,trans-farnesol. Resolution of racemic 14 was achieved via chromatographic separation of the diasteromeric camphonates. See ref 11 and (a) Jordine, C.; Bick, S.; Möller, U.; Welzel, P.; Daucher, B.; Maas, C. Tetrahedron 1994, 50, 139-160. (-)-Drimenol (14) can also be obtained from (-)-sclareol through drimenyl acetate in a five-step synthesis with 42% overall yield. See: (b) Barrero, A. F.; Alvarez-Manzaneda, E. J.: Altarejos, J.; Salido, S.; Ramos, J. M. Tetrahedron Lett. 1994, 35, 2945-2948. (c) Barrero, A. F.; Manzaneda, E. A.; Altarejos, J.; Salido, S.; Ramos, J. M.; Simmonds, M. J. S.; Blaney, W. M. Tetrahedron 1995, 51, 7435-7450.
    • (1995) Tetrahedron , vol.51 , pp. 7435-7450
    • Barrero, A.F.1    Manzaneda, E.A.2    Altarejos, J.3    Salido, S.4    Ramos, J.M.5    Simmonds, M.J.S.6    Blaney, W.M.7
  • 45
    • 17844372067 scopus 로고    scopus 로고
    • note
    • Compound 21b was also obtained after cyclization with camphosulfonic acid, under the conditions reported by Plumet et al. (see refs 9a and 10 and Supporting Information)
  • 46
    • 17844365681 scopus 로고    scopus 로고
    • note
    • See ref 9a for methylenedioxypuupehenol and its 8-epimer.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.