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Volumn , Issue 7, 2008, Pages 971-974

Synthesis of dictyopterene A

Author keywords

Boron; Cyclopropanes; Natural products; Stereoselectivity; Total synthesis

Indexed keywords

DICTYOPTERENE A; HYDROCARBON;

EID: 42949138445     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042918     Document Type: Article
Times cited : (16)

References (62)
  • 3
    • 0003870275 scopus 로고
    • Scheuer, P. J, Ed, Academic Press: New York, Chap. 2
    • (c) Moore, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1978, Chap. 2.
    • (1978) Marine Natural Products
    • Moore, R.E.1
  • 9
  • 20
    • 42949113187 scopus 로고    scopus 로고
    • Later, (1S,2S)-dictyopterene B enantiomer was discovered us a minor component in female gametes and essential oils of families Scytosiphonaceae, Chordariaceae, Dictyotaceae, see ref. 2m.
    • Later, (1S,2S)-dictyopterene B enantiomer was discovered us a minor component in female gametes and essential oils of families Scytosiphonaceae, Chordariaceae, Dictyotaceae, see ref. 2m.
  • 21
    • 85004559875 scopus 로고    scopus 로고
    • Optically pure dictyopterene A: (a) Kajiwara, T.; Nakatomi, T.; Sasaki, Y.; Hatanaka, A. Agric. Biol. Chem. 1980, 44, 2099.
    • Optically pure dictyopterene A: (a) Kajiwara, T.; Nakatomi, T.; Sasaki, Y.; Hatanaka, A. Agric. Biol. Chem. 1980, 44, 2099.
  • 27
    • 42949127750 scopus 로고    scopus 로고
    • Optically pure dictyopterene B: Dorch, D.; Kunz, E.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3319; and ref. 4a,b.
    • Optically pure dictyopterene B: Dorch, D.; Kunz, E.; Helmchen, G. Tetrahedron Lett. 1985, 26, 3319; and ref. 4a,b.
  • 28
    • 0001162575 scopus 로고    scopus 로고
    • Selected examples: (a) Yamada, K.; Tan, H.; Hirota, K. Tetrahedron Lett. 1980, 21, 4873.
    • Selected examples: (a) Yamada, K.; Tan, H.; Hirota, K. Tetrahedron Lett. 1980, 21, 4873.
  • 38
    • 0037547123 scopus 로고    scopus 로고
    • Thematic issue on cyclopropane chemistry (guest editor: A. de Meijere): Chem. Rev. 2002, 103, 931-1647.
    • Thematic issue on cyclopropane chemistry (guest editor: A. de Meijere): Chem. Rev. 2002, 103, 931-1647.
  • 53
    • 42949143247 scopus 로고    scopus 로고
    • Representative Procedure, Synthesis of E-olefin 6 To a stirred solution of the sulfone 7 (0.08 g, 0.28 mmol, 1.5 equiv) in anhyd DME (4 mL) at -60°C under N2 was added dropwise via cannula a solution of KHMDS (0.07 g, 0.34 mmol, 1.8 equiv) in anhyd DME (2 mL) over 5 min. The yellow-orange solution was stirred for 5 min and the aldehyde 3 (0.1 g, 0.19 mmol, 1 equiv) in anhyd DME (2 mL) was added dropwise via cannula over 5 min. The reaction mixture was stirred additional 10 min at -60°C and was then quenched with H2O (1 mL, The mixture was stirred vigorously whilst warming to r.t, diluted with Et2O (4 mL) and H2O (4 mL, and finally extracted with Et2O (3 x 4 mL, The combined organic layers were dried (MgSO4, filtered, and concentrated under reduced pressure. The crude product 6 was purified by flash column chromatography SiO2, petroleum ether-EtOAc, 95
    • ipso).
  • 58
    • 0037128484 scopus 로고    scopus 로고
    • Published racemate of oxaborinane 9: Markó, I. E.; Giard, T.; Sumida, S.; Gies, A.-E. Tetrahedron Lett. 2002, 43, 2317.
    • Published racemate of oxaborinane 9: Markó, I. E.; Giard, T.; Sumida, S.; Gies, A.-E. Tetrahedron Lett. 2002, 43, 2317.
  • 62
    • 42949132334 scopus 로고    scopus 로고
    • 1S,2S)-Dictyopterene A (1, α] D20 -69.3 (c 0.40, CHCl3, ref. 2d: [α]D22 +72 (c 6.74, CHCl3) for the 1R,2R-enantiomer. GC-MS (EI, 70 eV, m/z, 150 (100, M, 135 (15, M, CH3, 122 (24, M, C 2H4, 121 (60, M, C2H 5, 1H NMR (600 MHz, CDCl3, δ, 0.75-0.84 (m, 2 H, 3′-H, 0.87 (t, 3J 5″,6″, 7.0 Hz, 3 H, 6″-H, 1.25-1.35 (m, 4 H, 4″ and 5″-H, 1.36-1.41 (m, 2 H, 1′-H and 2′-H, 1.95-2.05 (m, 2 H, 3″-H, 4.84 (dd, 3J1,2, 10.2 Hz, 2J2a,2b, 2.3 Hz, 1 H, 2-Ha, 4.98 dd, 3J1,2, 17.2 Hz, 2 J2a,2b, 2.3 Hz
    • 3): δ = 14.1 (C-6″), 14.8 (C-3′), 22.3 (C-5″), 23.6 (C-2′), 24.3 (C-1′), 31.8 (C-4″), 32.2 (C-3″), 111.8 (C-2), 129.2 (C-2″), 131.6 (C-1″), 140.9 (C-1).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.