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Volumn 43, Issue 24, 2002, Pages 4361-4364

Controlled syntheses of 12-oxo-PDA and its 13-epimer

Author keywords

12 oxo PDA; Asymmetric synthesis; Copper catalyst; Coupling reaction; Cyclopenten 1,3 diol monoacetate

Indexed keywords

12 OXOPHYTODIENOIC ACID; 13 EPI 12 OXOPHYTODIENOIC ACID; ACETIC ACID DERIVATIVE; ACID; COPPER; CYCLOPENTEN 1,3 DIOL MONOACETATE; CYCLOPENTENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037053850     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)00786-4     Document Type: Article
Times cited : (14)

References (33)
  • 16
    • 0005993653 scopus 로고    scopus 로고
    • 2Si group was partially deprotected with Jones reagent
  • 18
    • 0005915072 scopus 로고    scopus 로고
    • The regioisomer 18 was synthesized from 3 regioselectively by using the reagent derived from 6 (3 equiv.) and CuCN (3.5 equiv.) in THF at 0°C for 5 h
  • 20
    • 0005987005 scopus 로고    scopus 로고
    • note
  • 24
    • 0005915840 scopus 로고    scopus 로고
    • Ref.4c
  • 26
    • 0005987006 scopus 로고    scopus 로고
    • note
  • 28
    • 0005983903 scopus 로고    scopus 로고
    • 3) spectra of 1 and 2 are protons at C(11) and C(10): 1, δ 6.19 (dd, J=6, 1.5 Hz, 1H), 7.74 (dd, J=6, 3 Hz, 1H); 2, δ 6.13 (dd, J=6, 2 Hz, 1H), 7.61 (dd, J=6, 2.5 Hz, 1H)
  • 32
    • 0005954756 scopus 로고    scopus 로고
    • 3 before use
  • 33
    • 0005915073 scopus 로고    scopus 로고
    • Since the stability of 1 under the almost neutral conditions is established, it might be likely that the strongly acidic conditions of Jones oxidation to produce 1 and subsequent purification by silica gel chromatography brought about epimerization of 1, but to a small extent (<5%)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.