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Volumn 52, Issue 17, 2011, Pages 2088-2092

Exploration of a proposed biomimetic synthetic route to plumarellide. Development of a facile transannular Diels-Alder reaction from a macrocyclic enedione leading to a new 5,6,7-tricyclic ring system

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; FURAN DERIVATIVE; MACROCYCLIC COMPOUND; PLUMARELLIDE; UNCLASSIFIED DRUG;

EID: 79251497725     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.10.154     Document Type: Article
Times cited : (27)

References (28)
  • 8
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    • For a recent summary of cembranoid enedione natural products found in corals, see
    • For a recent summary of cembranoid enedione natural products found in corals, see: Roethle, P. A.; Trauner, D. Nat. Prod. Rep. 2008, 25, 298-317;
    • (2008) Nat. Prod. Rep. , vol.25 , pp. 298-317
    • Roethle, P.A.1    Trauner, D.2
  • 11
    • 0030041294 scopus 로고    scopus 로고
    • Two 12-membered ring 'pseudopterane' diterpenes containing a Zalkenylbutenolide moiety are known, see
    • Two 12-membered ring 'pseudopterane' diterpenes containing a Zalkenylbutenolide moiety are known, see: Rodríguez, A. D.; Soto, J. J. Chem. Pharm. Bull. 1996, 44, 91-94;
    • (1996) J. Chem. Pharm. Bull. , vol.44 , pp. 91-94
    • Rodríguez, A.D.1    Soto, J.2
  • 13
    • 79953241545 scopus 로고    scopus 로고
    • See: (a) Refs. 2 and 8
    • See: (a) Refs. 2 and 8.;
  • 15
    • 79953252944 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra. Interestingly, they were shown to be epimeric at the t-hydroxy centre in their cyclopentane rings, although a direct comparison has not been forthcoming; see Refs. 1 and 2. (b) In this proof-of-principle study we have used the diastereoisomer 10 of the starting material which has the same stereochemistry at the t-hydroxy centre in mandapamate, but is epimeric with the same centre in plumarellide. (c) The model compounds 8b and 8c, lacking the C-1 propenyl group present in natural cembranoids, were chosen for synthesis expediency.
  • 22
    • 79953254295 scopus 로고    scopus 로고
    • note
    • 3)
  • 23
    • 0035858717 scopus 로고    scopus 로고
    • 1H proton coupling data. Reference to the seminal studies of Deslongchamps et al. on the transannular Diels-Alder reaction and the predicted outcome of the sterochemistries of adducts from isomeric diene and dienophile precursors would suggest that the cis, anti, cis geometry associated with the substituted cyclohexane ring in 27 would most likely arise from the precursors 24/25 accommodating an E-dienophile. See: This analysis may be flawed however for several reasons, including the possibilities for post epimerisations of labile C-H centres in 26/27
    • 1H proton coupling data. Reference to the seminal studies of Deslongchamps et al. on the transannular Diels-Alder reaction and the predicted outcome of the sterochemistries of adducts from isomeric diene and dienophile precursors would suggest that the cis, anti, cis geometry associated with the substituted cyclohexane ring in 27 would most likely arise from the precursors 24/25 accommodating an E-dienophile. See: Marsault, E.; Toró, A.; Nowak, P.; Deslongchamps, P. Tetrahedron 2001, 57, 4243-4260. This analysis may be flawed however for several reasons, including the possibilities for post epimerisations of labile C-H centres in 26/27.
    • (2001) Tetrahedron , vol.57 , pp. 4243-4260
    • Marsault, E.1    Toró, A.2    Nowak, P.3    Deslongchamps, P.4
  • 26
    • 65349153731 scopus 로고    scopus 로고
    • For recent synthetic studies with cyathane diterpenes, see
    • For recent synthetic studies with cyathane diterpenes, see: Enquist, J. A.; Stoltz, B. M. Nat. Prod. Rep. 2009, 26, 661-680.
    • (2009) Nat. Prod. Rep. , vol.26 , pp. 661-680
    • Enquist, J.A.1    Stoltz, B.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.