메뉴 건너뛰기




Volumn 128, Issue 51, 2006, Pages 16989-16999

Total synthesis, structure revision, and absolute configuration of (-)-brevenal

Author keywords

[No Author keywords available]

Indexed keywords

CONVERGENT ASSEMBLY; PENTACYCLIC POLYETHER SKELETON; STILLE COUPLING; SUZUKI MIYAURA COUPLING CHEMISTRY;

EID: 33845963639     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066772y     Document Type: Article
Times cited : (120)

References (81)
  • 1
    • 1542502091 scopus 로고
    • For reviews on marine polycyclic ethers, see: a
    • For reviews on marine polycyclic ethers, see: (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
    • (1993) Chem. Rev , vol.93 , pp. 1897-1909
    • Yasumoto, T.1    Murata, M.2
  • 4
    • 30744459350 scopus 로고    scopus 로고
    • For recent comprehensive reviews on total synthesis of polycyclic ethers. see: a
    • For recent comprehensive reviews on total synthesis of polycyclic ethers. see: (a) Nakata, T. Chem. Rev. 2005, 105, 4314-4347.
    • (2005) Chem. Rev , vol.105 , pp. 4314-4347
    • Nakata, T.1
  • 5
    • 30744476469 scopus 로고    scopus 로고
    • (b) Inoue, M. Chem. Rev. 2005, 105, 4379-4405.
    • (2005) Chem. Rev , vol.105 , pp. 4379-4405
    • Inoue, M.1
  • 16
    • 33746588648 scopus 로고    scopus 로고
    • For a preliminary communication, see
    • For a preliminary communication, see: Fuwa, H.; Bbine. M.; Sasaki, M. J. Am. Chem. Soc. 2006, 128, 9648-9650.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 9648-9650
    • Fuwa, H.1    Bbine, M.2    Sasaki, M.3
  • 21
    • 14344266665 scopus 로고    scopus 로고
    • 2nd ed, de Meijere, A, Diederich, F, Eds, Wiley-VCH: Weinheim
    • (c) Mitchell, T. C. In Metal-catalyzed Cross-coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004: pp 125-162.
    • (2004) Metal-catalyzed Cross-coupling Reactions , pp. 125-162
    • Mitchell, T.C.1
  • 23
    • 2042507954 scopus 로고
    • For reviews on Suzuki-Miyaura coupling, see: a
    • For reviews on Suzuki-Miyaura coupling, see: (a) Suzuki, A.; Miyaura, N. Chem. Rev. 1995, 95, 2457-2483.
    • (1995) Chem. Rev , vol.95 , pp. 2457-2483
    • Suzuki, A.1    Miyaura, N.2
  • 48
    • 33845936004 scopus 로고    scopus 로고
    • The carbon numbering of all compounds in this paper corresponds to that of brevenal
    • The carbon numbering of all compounds in this paper corresponds to that of brevenal.
  • 59
    • 33845941394 scopus 로고    scopus 로고
    • The reaction mixture was stirred at room temperature overnight (ca. 13 h). Since, at this point, ca. 50% of the starting material 48 remained unreacted and a small amount of diol S8 was observed by TLC analysis, the reaction was quenched. After separation of 48, 49, S8, and S7 by flash chromatocraphy, recycling of the recovered 48 (three times) provided 49 (78%), S8 (8%) and S7 (12%). (Equation Presented)
    • The reaction mixture was stirred at room temperature overnight (ca. 13 h). Since, at this point, ca. 50% of the starting material 48 remained unreacted and a small amount of diol S8 was observed by TLC analysis, the reaction was quenched. After separation of 48, 49, S8, and S7 by flash chromatocraphy, recycling of the recovered 48 (three times) provided 49 (78%), S8 (8%) and S7 (12%). (Equation Presented)
  • 66
    • 33845961706 scopus 로고    scopus 로고
    • We initially attempted the Stille coupling of TBDPS-protected vinyl stannane 5a with vinyl iodide 3; however, the desired cross-coupled product was obtained in only poor yield 22
    • We initially attempted the Stille coupling of TBDPS-protected vinyl stannane 5a with vinyl iodide 3; however, the desired cross-coupled product was obtained in only poor yield (22%).
  • 69
    • 0021860657 scopus 로고
    • (a) Nakanishi, K. Toxicon 1985, 23, 473-479.
    • (1985) Toxicon , vol.23 , pp. 473-479
    • Nakanishi, K.1
  • 76
    • 11144320327 scopus 로고    scopus 로고
    • For recent reviews on biomimetic synthesis of polycyclic ethers, see: a
    • For recent reviews on biomimetic synthesis of polycyclic ethers, see: (a) Fujiwara, K.; Murai, A. Bull. Chem. Soc. Jpn. 2004, 77, 2129-2146.
    • (2004) Bull. Chem. Soc. Jpn , vol.77 , pp. 2129-2146
    • Fujiwara, K.1    Murai, A.2
  • 78
    • 85083243520 scopus 로고
    • For a review, see
    • For a review, see: Tsuji, J. Synthesis 1984, 369-384.
    • (1984) Synthesis , pp. 369-384
    • Tsuji, J.1
  • 79
    • 0032569909 scopus 로고    scopus 로고
    • Smith, A. B., III: Cho, Y. S.; Friestad, G. K. Tetrahedron Lett. 1998, 39, 8765-8768.
    • Smith, A. B., III: Cho, Y. S.; Friestad, G. K. Tetrahedron Lett. 1998, 39, 8765-8768.
  • 80
    • 0037241493 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: (a) Weinreb, S. M. Acc. Chem. Res. 2003, 36, 59-65.
    • (2003) Acc. Chem. Res , vol.36 , pp. 59-65
    • Weinreb, S.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.