메뉴 건너뛰기




Volumn 64, Issue 35, 2008, Pages 8134-8140

Stereodivergent reduction of enelactams embedded in hexahydroindoles. Synthesis of trans-3-substituted-cis-3a-methyloctahydroindoles

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALKALOID; AMIDE; INDOLE DERIVATIVE; LACTAM DERIVATIVE;

EID: 47049088738     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.055     Document Type: Article
Times cited : (10)

References (34)
  • 4
    • 65949110312 scopus 로고    scopus 로고
    • Daphniphyllum Alkaloids: Structures, Biogenesis, and Activities
    • Fattorusso E., and Taglilatela-Scafati O. (Eds), Wiley-VCH, Weinheim
    • Morita H., and Kobayashi J. Daphniphyllum Alkaloids: Structures, Biogenesis, and Activities. In: Fattorusso E., and Taglilatela-Scafati O. (Eds). Modern Alkaloids: Structure, Isolation, Synthesis and Biology (2008), Wiley-VCH, Weinheim
    • (2008) Modern Alkaloids: Structure, Isolation, Synthesis and Biology
    • Morita, H.1    Kobayashi, J.2
  • 5
    • 47049094554 scopus 로고    scopus 로고
    • note
    • 6
  • 16
    • 47049107895 scopus 로고    scopus 로고
    • For other synthetic approaches to the synthesis of 3a-methyl-cis-octahydroindoles with a trans substituent at C-3, see:
    • For other synthetic approaches to the synthesis of 3a-methyl-cis-octahydroindoles with a trans substituent at C-3, see:
  • 20
    • 47049109924 scopus 로고    scopus 로고
    • See Ref. 1b.
    • See Ref. 1b.
  • 22
    • 40049107836 scopus 로고    scopus 로고
    • For the synthesis of 2,6-dioxo-1,2,3,4,5,6-hexahydroindole derivatives, see:
    • For the synthesis of 2,6-dioxo-1,2,3,4,5,6-hexahydroindole derivatives, see:. Juma B., Adeel M., Villinger A., and Langer P. Tetrahedron Lett. 49 (2008) 2272-2274
    • (2008) Tetrahedron Lett. , vol.49 , pp. 2272-2274
    • Juma, B.1    Adeel, M.2    Villinger, A.3    Langer, P.4
  • 24
    • 47049088608 scopus 로고    scopus 로고
    • note
    • 3 in the reduction of enamide 10 a 4:1 mixture of trans derivative 12 and its C-7a epimer 15 was obtained.
  • 25
    • 34347323943 scopus 로고    scopus 로고
    • For a hydrogenation process in a related N-(Boc)hexahydroindole derivative, see:
    • For a hydrogenation process in a related N-(Boc)hexahydroindole derivative, see:. Keaney G.F., and Johannes C.W. Tetrahedron Lett. 48 (2007) 5411-5413
    • (2007) Tetrahedron Lett. , vol.48 , pp. 5411-5413
    • Keaney, G.F.1    Johannes, C.W.2
  • 27
    • 34247644854 scopus 로고    scopus 로고
    • For a different stereoselectivity either in hydrogenation processes or in hydride reductions in an acid medium in related 3a-arylhexahydroindol-2-ones, see:
    • For a different stereoselectivity either in hydrogenation processes or in hydride reductions in an acid medium in related 3a-arylhexahydroindol-2-ones, see:. Saito M., Matsuo J., and Ishibashi H. Tetrahedron 63 (2007) 4865-4873
    • (2007) Tetrahedron , vol.63 , pp. 4865-4873
    • Saito, M.1    Matsuo, J.2    Ishibashi, H.3
  • 29
    • 47049098677 scopus 로고    scopus 로고
    • note
    • Although a coordination of the hydroxyethyl group with the reducing agent could be considered to justify the cis diastereoselectivity in the reduction of iminium A to 6, the same substrate-directable effect should be observed in the reduction of alcohol 10, but in this case, and under the same reaction conditions, it resulted in a trans diastereoselectivity (10→12).{A figure is presented}
  • 30
    • 47049095067 scopus 로고    scopus 로고
    • For NMR studies about cis- and trans-3a-substituted octahydroindole derivatives, see:
    • For NMR studies about cis- and trans-3a-substituted octahydroindole derivatives, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.