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Volumn 10, Issue 7, 2008, Pages 1401-1404

Synthesis of (±)-vibralactone

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE; VIBRALACTONE;

EID: 45849108811     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800118c     Document Type: Article
Times cited : (45)

References (29)
  • 3
    • 1242321874 scopus 로고    scopus 로고
    • Chem. Abstr. 2001, 287595.
    • (2001) Chem. Abstr , pp. 287595
  • 4
  • 5
    • 0027175468 scopus 로고
    • For reviews on β-lactones, see: a
    • For reviews on β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-459.
    • (1993) Synthesis , pp. 441-459
    • Pommier, A.1    Pons, J.-M.2
  • 16
    • 59849114330 scopus 로고    scopus 로고
    • The stereochemistry of alcohols 5 and 6 was established by an IR study in dilute (0.1 M) CCl4 solution and a 1D NOESY experiment. Trans hydroxy ester 6 showed two equally intense peaks at 1734 cm-1 (free carbonyl) and 1711 cm-1 (hydrogen bonded carbonyl, whereas cis hydroxy ester 5 showed one medium peak at 1734 cm-1 (free carbonyl) and a very strong peak at 1716 cm-1 (hydrogen bonded carbonyl).9 In a 1D NOESY experiment, irradiation of the CHOH hydrogen at δ 4.14 in 6 showed NOEs to the hydroxy hydrogen at δ 2.77 and the ring hydrogens at δ 1.88-1.76. Irradiation of the CHOH hydrogen at δ 3.79 in 5 showed NOEs to the hydroxy hydrogen at δ 3.28 and the allylic side chain methylene group at δ 2.52-2.40 establishing that the hydrogen is cis to the prenyl side chain
    • 9 In a 1D NOESY experiment, irradiation of the CHOH hydrogen at δ 4.14 in 6 showed NOEs to the hydroxy hydrogen at δ 2.77 and the ring hydrogens at δ 1.88-1.76. Irradiation of the CHOH hydrogen at δ 3.79 in 5 showed NOEs to the hydroxy hydrogen at δ 3.28 and the allylic side chain methylene group at δ 2.52-2.40 establishing that the hydrogen is cis to the prenyl side chain.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.