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Volumn 54, Issue 38, 1998, Pages 11421-11430

A convenient synthesis of (2s,3r,6s,7z)- and (2r,3s,6s,7z)-2,3-epoxy- 7,10-bisaboladiene, the sex pheromones of the southern green stink bug (nezara viridula)

Author keywords

Olefination; Pheromones; Sulfur compound; Terpenes and terpenoids

Indexed keywords

2,3 EPOXY 7,10 BISABOLADIENE; NEROLIDOL; SEX PHEROMONE; SULFUR; TERPENE; UNCLASSIFIED DRUG;

EID: 0032541592     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00696-6     Document Type: Article
Times cited : (6)

References (31)
  • 26
    • 37049103873 scopus 로고
    • 26. The erythro-phenylthio alcohol (erythro-20, a mixture of two erythro-diastereomers) was converted stereospecifically to the (E)-isomer of 1 by the same treatment. This fact supports our assignments of the relative stereochemistries for threo-20 and erythro-20. For similar threo-selective addition of a hydride ion to α-phenylthio or α-methylthio ketones, see: Brownbridge, P.; Egert, E.; Hunt, P. G.; Kennard, O.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1981, 2751-2759; Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775-4778.
    • (1981) J. Chem. Soc., Perkin Trans. 1 , pp. 2751-2759
    • Brownbridge, P.1    Egert, E.2    Hunt, P.G.3    Kennard, O.4    Warren, S.5
  • 27
    • 0000822952 scopus 로고
    • 26. The erythro-phenylthio alcohol (erythro-20, a mixture of two erythro-diastereomers) was converted stereospecifically to the (E)-isomer of 1 by the same treatment. This fact supports our assignments of the relative stereochemistries for threo-20 and erythro-20. For similar threo-selective addition of a hydride ion to α-phenylthio or α-methylthio ketones, see: Brownbridge, P.; Egert, E.; Hunt, P. G.; Kennard, O.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1981, 2751-2759; Shimagaki, M.; Maeda, T.; Matsuzaki, Y.; Hori, I.; Nakata, T.; Oishi, T. Tetrahedron Lett. 1984, 25, 4775-4778.
    • (1984) Tetrahedron Lett. , vol.25 , pp. 4775-4778
    • Shimagaki, M.1    Maeda, T.2    Matsuzaki, Y.3    Hori, I.4    Nakata, T.5    Oishi, T.6
  • 29
    • 85038549788 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of 22a, 23, and 24. The equatorially oriented C-2 proton of 22a and 23 both appeared as a broad singlet with small unresolved couplings (at δ 3.63 and δ 4.80, respectively). On the other hand, the axially oriented C-2 proton of 24 was observed as a double doublet ( at δ 3.85, J = 12.0, 5.0 Hz).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.