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Volumn 2003, Issue 8, 2003, Pages 45-57

Enantioselective total synthesis of (+)-aureol via aBF3·Et2O-promoted rearrangement/cyclizationreaction of (+)-arenarol

Author keywords

Arenarol; Aureol; Marine natural product; Rearrangement; Total synthesis

Indexed keywords

2 (DECAHYDRO 1BETA,2BETA,4AALPHA TRIMETHYL 5 METHYLENE NAPHTHALEN 1 YL METHYL)PHENOL; 2 LITHIOANISOLE; ANISOLE DERIVATIVE; ARENAROL; ARENARONE; AUREOL; BENZOQUINONE DERIVATIVE; BORON TRIFLUORIDE; CYTOTOXIC AGENT; DECAHYDRO 1ALPHA [1 HYDROXY (2 METHOXYPHENYL)METHYL] 1BETA,2BETA,4AALPHA TRIMETHYL 5 (1,3 DIOXOLAN 2YL)NAPHTHALENE; DECALIN DERIVATIVE; ETHER; NAPHTHALENE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 3242683254     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (14)

References (37)
  • 1
    • 0036007872 scopus 로고    scopus 로고
    • For recent excellent reviews on the clerodane diterpenoids and related compounds including marine natural products, see: (a) Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1.
    • (2002) J. Nat. Prod. Rep. , vol.19 , pp. 1
    • Faulkner, D.1
  • 4
    • 77957087867 scopus 로고
    • Attaur-Rahman., Ed.; Elsevier Science B.V.: Amsterdam
    • (d) Capon, R. J. in Studies in Natural Products Chemistry; Attaur-Rahman., Ed.; Elsevier Science B.V.: Amsterdam, 1995; Vol. 15, p. 289.
    • (1995) Studies in Natural Products Chemistry , vol.15 , pp. 289
    • Capon, R.J.1
  • 8
    • 3242675720 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
  • 9
    • 3242736293 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.
  • 16
    • 0035965756 scopus 로고    scopus 로고
    • In 2001, Waldmann and co-workers 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 products; therefore, detailed information regarding the stereoselectivity, yield, and reaction conditions for this rearrangement was not given. See: Stahl, P.; Kissau, L.; Mazitschek, R.; Huwe, A.; Furet, P.; Giannis, A.; Waldmann, H. J. Am. Chem. Soc. 2001, 123, 11586.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11586
    • Stahl, P.1    Kissau, L.2    Mazitschek, R.3    Huwe, A.4    Furet, P.5    Giannis, A.6    Waldmann, H.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.