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Volumn 70, Issue 15, 2005, Pages 6045-6052

Total syntheses of naturally occurring diacetylenic spiroacetal enol ethers

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; PALLADIUM; SYNTHESIS (CHEMICAL);

EID: 22244477358     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo050822k     Document Type: Article
Times cited : (34)

References (44)
  • 12
    • 32744457714 scopus 로고    scopus 로고
    • note
    • According to the IUPAC nomenclature system, (-)-AL-2 (2) should be described as (-)-(2E,3S,4R,5R)-3,4-epoxy-2-(2,4-hexadiynylidene)-1,6- dioxaspiro[4.5]decane. This numbering system is used for the dioxaspiro compounds in this paper.
  • 23
    • 0020850942 scopus 로고
    • For similar palladiumd(II)-catalyzed reactions, see: (a) Utimoto, K. Pure Appl. Chem. 1983, 54, 1845-1852.
    • (1983) Pure Appl. Chem. , vol.54 , pp. 1845-1852
    • Utimoto, K.1
  • 29
    • 32744466096 scopus 로고    scopus 로고
    • note
    • 13C NMR experiments. See ref 8.
  • 30
    • 0141629681 scopus 로고    scopus 로고
    • Part of this work was published as a preliminary communication: Miyakoshi, N.; Mukai, C. Org. Lett. 2003, 5, 2335-2338.
    • (2003) Org. Lett. , vol.5 , pp. 2335-2338
    • Miyakoshi, N.1    Mukai, C.2
  • 34
    • 32744469148 scopus 로고    scopus 로고
    • note
    • A mixture of two diastereoisomers was obtained.
  • 35
    • 32744462566 scopus 로고    scopus 로고
    • note
    • The structure of 22 was elucidated by spectral evidence. In particular, NOE experiments revealed no enhancement between the vinylic proton and H-3 or between H-4 and H-10. In the 4-related (4R,5S)-compounds, an enhancement between H-4 and H-10 was observed in the NOE experiments.
  • 38
    • 32744463742 scopus 로고    scopus 로고
    • note
    • Ohigashi and co-workers reported preparation of compound 6 from naturally occurring AL-2 (2) and ent-3 by successive reduction, tosylation, and olefin formation reaction. However, no description concerning to its specific rotation could be available. See ref 1h.
  • 40
    • 32744459490 scopus 로고    scopus 로고
    • note
    • Ohigashi and co-workers isolated 1 mg of (+)-3 when 4.2 mg of (-)-AL-2 (2) was exposed to the same acidic conditions. See ref 1h.
  • 42
    • 32744467961 scopus 로고    scopus 로고
    • note
    • 3-position when treated with 10% hydrochloric acid in methanol. See ref 1h.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.