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Volumn , Issue 13, 2004, Pages 2379-2381

Synthesis of C-13 oxidised cuparene and herbertane sesquiterpenes via a Paternò-Büchi photocyclisation-oxetane fragmentation strategy: Total synthesis of 1,13-herbertenediol

Author keywords

Fused ring systems; Photochemistry; Reduction; Ring opening; Terpenoids

Indexed keywords

1,13 HERBERTENEDIOL; CUPARENE; CYCLOPENTANE; HERBERTANE; METHYL GROUP; OXETANE DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 8644243047     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832813     Document Type: Article
Times cited : (19)

References (29)
  • 17
    • 0034710512 scopus 로고    scopus 로고
    • and references therein
    • The combination of a Paternò-Büchi reaction and selective oxetane cleavage has found notable application in the synthesis of triquinane natural products. See: Reddy, T. J.; Rawal, V. H. Org. Lett. 2000, 2, 2711; and references therein.
    • (2000) Org. Lett. , vol.2 , pp. 2711
    • Reddy, T.J.1    Rawal, V.H.2
  • 20
    • 0037067558 scopus 로고    scopus 로고
    • Recently LDBB has been shown to partially reduce certain electron-deficient aromatic compounds: Donohoe, T. J.; House, D. J. Org. Chem. 2002, 67, 5015. We have not observed formation of any Birch-type products, consistent with the electron-rich nature of the aromatic ring in the systems under investigation.
    • (2002) J. Org. Chem. , vol.67 , pp. 5015
    • Donohoe, T.J.1    House, D.2
  • 23
    • 8644252205 scopus 로고    scopus 로고
    • note
    • Attempted preparation of the photochemical precursor 14 via an analogous sequence of reactions to that described in Scheme 1 was thwarted by the formation of 19 as the major product upon attempted Wittig olefination of 18. Alkene 19 is presumably formed by an initial retro-Michael addition under the reactions conditions to reform ketone 8, which subsequently undergoes Wittig olefination. The sluggish reactivity of hindered aryl ketones to the phosphorus ylide necessitates the high temperature employed, although the difference in reactivity of 2 and 18 under identical reaction conditions is notable. To date, we have been unable to achive methylation of 18 using other methods (Scheme 3). (Diagram presented)
  • 24
    • 8644279149 scopus 로고    scopus 로고
    • note
    • 2Na requires 271.1669). MS (EI): m/z (%) = 248 (54), 218 (20), 217 (95), 187 (44), 161 (42), 135 (100), 105 (19), 95(17), 69 (29) and 41 (11).
  • 29
    • 8644240459 scopus 로고    scopus 로고
    • note
    • 4 and concentrated in vacuo to furnish a pale yellow oil. The crude product was purified by column chromatography (hexane-EtOAc 9:1) to afford 1,13-herbertenediol as a colourless oil (29 mg, 77%). Analytic data agree with those reported in the literature.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.