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Volumn 43, Issue 39, 2002, Pages 6929-6932

An efficient synthesis of (+)-aureol via boron trifluoride etherate-promoted rearrangement of (+)-arenarol

Author keywords

Arenarol; Aureol; Domino reaction; Marine natural product; Rearrangement

Indexed keywords

ALCOHOL DERIVATIVE; ARENAROL; AUREOL; BORON TRIFLUORIDE; UNCLASSIFIED DRUG;

EID: 0037163283     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01627-1     Document Type: Article
Times cited : (53)

References (27)
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    • 0034032999 scopus 로고    scopus 로고
    • For recent excellent reviews on the clerodane diterpenoids and related compounds including marine natural products, see: (a) Tokoroyama, T. Synthesis 2000, 611-623; (b) Capon, R. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, 1995; Vol. 15, pp. 289-326.
    • (2000) Synthesis , pp. 611-623
    • Tokoroyama, T.1
  • 2
    • 77957087867 scopus 로고
    • Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam
    • For recent excellent reviews on the clerodane diterpenoids and related compounds including marine natural products, see: (a) Tokoroyama, T. Synthesis 2000, 611-623; (b) Capon, R. J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science B.V.: Amsterdam, 1995; Vol. 15, pp. 289-326.
    • (1995) Studies in Natural Products Chemistry , vol.15 , pp. 289-326
    • Capon, R.J.1
  • 5
    • 0005198041 scopus 로고    scopus 로고
    • (Harbor Branch Oceanographics Institution, Inc., USA). PCT WO 9112250 A1, August 22, 1991
    • Wright, A. E.; Cross, S. S.; Burres, N. S.; Koehn, F. (Harbor Branch Oceanographics Institution, Inc., USA). PCT WO 9112250 A1, August 22, 1991.
    • Wright, A.E.1    Cross, S.S.2    Burres, N.S.3    Koehn, F.4
  • 6
    • 0005165989 scopus 로고    scopus 로고
    • note
    • It was reported that aureol (1) was isolated in 0.036% yield (dry weight) from the marine sponge Smenospongia aurea, see Ref. 2.
  • 10
    • 0035965756 scopus 로고    scopus 로고
    • Quite recently, Waldmann et al. reported an analogous rearrangement reaction in their total synthesis of nakijiquinones, novel marine sesquiterpene quinones. In this work, the rearrangement products related to 1 and 3 were regarded as undesired and useless compounds; hence, a detailed description including the stereoselectivity, yield, and reaction conditions for this rearrangement was not provided. See: Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586-11593.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11586-11593
    • Stahl, P.1    Kissau, L.2    Mazitschek, R.3    Huwe, A.4    Furet, P.5    Giannis, A.6    Waldmann, H.7
  • 13
    • 0034714389 scopus 로고    scopus 로고
    • Recently, we noticed that Kobayashi and co-workers also encountered similar CAN oxidation problems in their synthetic studies on akaterpin, a novel marine natural product, see: Kawai N., Fujibayashi Y., Kuwabara S., Takao K., Ijuin Y., Kobayashi S. Tetrahedron. 56:2000;6467-6478.
    • (2000) Tetrahedron , vol.56 , pp. 6467-6478
    • Kawai, N.1    Fujibayashi, Y.2    Kuwabara, S.3    Takao, K.4    Ijuin, Y.5    Kobayashi, S.6
  • 26
    • 0005161869 scopus 로고    scopus 로고
    • note
    • To obtain theoretical support for the rearrangement/cyclization event, we carried out computational studies with Gaussian 98 program ( Ref. 17 ). The structural optimizations of the compounds 1 and 3 were carried out by the B3LYP DFT (density functional theory) using 6-31G(D) as a basis set. The calculations estimate that the trans-fused decalin compound 3 is 6.67 kcal/mol more stable than aureol (1) possessing the cis-fused decalin system.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.