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Volumn 64, Issue 12, 1999, Pages 4560-4563

[5 + 2] Pyrone-alkene cycloaddition approach to tetrahydrofurans. Expeditious synthesis of (±)-nemorensic acid

Author keywords

[No Author keywords available]

Indexed keywords

NEMORENSIC ACID; PYRONE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0039738834     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990233c     Document Type: Article
Times cited : (45)

References (26)
  • 3
    • 0001815816 scopus 로고    scopus 로고
    • (c) Chem. Rev. 1996, 96, 1.
    • (1996) Chem. Rev. , vol.96 , pp. 1
  • 14
    • 0001104144 scopus 로고
    • Manske, R. H. F., Ed.; Academic Press: New York, Chapter 14
    • Warren, F. L. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1970; Vol. 12, Chapter 14.
    • (1970) The Alkaloids , vol.12
    • Warren, F.L.1
  • 16
    • 0023739046 scopus 로고
    • (b) Klein, L. L.; Shanklin, M. S. J. Org. Chem. 1988, 53, 5202. Recently, an asymmetric synthesis from acyclic precursors of (+)-nemorensic acid has been described:
    • (1988) J. Org. Chem. , vol.53 , pp. 5202
    • Klein, L.L.1    Shanklin, M.S.2
  • 20
    • 0002241276 scopus 로고
    • It is known that activated Raney nickel can reduce ketones; see: (a) Takahashi, T.; Kitano, K.; Hagi, T.; Nihomantsu, H. Chem. Lett. 1989, 597. (b) Caubére, P.; Coutrut, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: New York, 1991; Vol. 8, Chapter 4.3 and references given therein.
    • (1989) Chem. Lett. , pp. 597
    • Takahashi, T.1    Kitano, K.2    Hagi, T.3    Nihomantsu, H.4
  • 21
    • 0003417469 scopus 로고
    • Trost, B. M., Fleming, I., Eds; Pergamon: New York, Chapter 4.3 and references given therein
    • It is known that activated Raney nickel can reduce ketones; see: (a) Takahashi, T.; Kitano, K.; Hagi, T.; Nihomantsu, H. Chem. Lett. 1989, 597. (b) Caubére, P.; Coutrut, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon: New York, 1991; Vol. 8, Chapter 4.3 and references given therein.
    • (1991) Comprehensive Organic Synthesis , vol.8
    • Caubére, P.1    Coutrut, P.2
  • 26
    • 0345177189 scopus 로고    scopus 로고
    • note
    • Attachment of allylmercaptan to the bromide can be carried out more efficiently (in approximately 85% yield) if the pyrone hydroxyl is protected prior to the reaction as the PMB ether, although this protocol introduces two additional steps into the synthesis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.