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Volumn , Issue 4, 2005, Pages 591-594

Sulfanyl radical-induced cyclization of linalyl acetate to the iridane skeleton: A short synthesis of (±)-dehydroiridomyrmecin

Author keywords

Addition cyclization reaction; Dehydroiridomyrmecin; Iridane skeleton; Polyprenes; Sulfanyl radical

Indexed keywords

ACETIC ACID DERIVATIVE; DEHYDROIRIDOMYRMECIN; LINALYL ACETATE; RADICAL; SUFANYL RADICAL; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 15444375348     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-863729     Document Type: Article
Times cited : (13)

References (60)
  • 1
    • 0004269715 scopus 로고    scopus 로고
    • Renaud, P.; Sibi, P., Eds.; Wiley-VCH: Weinheim
    • (a) Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Sibi, P., Eds.; Wiley-VCH: Weinheim, 2001.
    • (2001) Radicals in Organic Synthesis , vol.1
  • 2
    • 0004269715 scopus 로고    scopus 로고
    • Renaud, P.; Sibi, P., Eds.; Wiley-VCH: Weinheim
    • (b) Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi, P., Eds.; Wiley-VCH: Weinheim, 2001.
    • (2001) Radicals in Organic Synthesis , vol.2
  • 21
    • 0001060282 scopus 로고    scopus 로고
    • Sulfur-centered radicals
    • Renaud, P.; Sibi, P., Eds.; Wiley-VCH: Weinheim
    • (a) Bertrand, P.; Ferreri, C. Sulfur-Centered Radicals, In Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi, P., Eds.; Wiley-VCH: Weinheim, 2001, 485-504.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 485-504
    • Bertrand, P.1    Ferreri, C.2
  • 41
    • 15444369675 scopus 로고    scopus 로고
    • note
    • The products 4, 5, 6, 9, 10, 11 (see Table 1) were obtained as an unseparable mixture of diastereoisomers using conventional chromatography.
  • 45
    • 15444371608 scopus 로고    scopus 로고
    • note
    • General Procedure for Radical Cyclization (4, 5, 6, 9, 10, 11). A solution of thiophenol (0.18 mL, 1.66 mmol) and AIBN (136 mg, 0.83 mmol) in benzene (16 mL) was added dropwise (8 mL/h) under an argon atmosphere to a boiling solution of 3 (200 mg, 0.83 mmol) in benzene (8 mL). The solvent was evaporated under reduced pressure. Purification of the residue by column chromatography (hexane-t-BuOMe, 20:1) afforded 9, 262 mg (90%, see Table 1).
  • 51
    • 15444370368 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra were identical to those reported in the literature.
  • 55
    • 15444364480 scopus 로고    scopus 로고
    • note
    • +: 313.1238; found: 313.1239.
  • 58
    • 15444369489 scopus 로고    scopus 로고
    • note
    • (b) 5% of sulfone was obtained.
  • 60
    • 15444380118 scopus 로고    scopus 로고
    • note
    • +: 167.1072; found: 167.1070.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.