메뉴 건너뛰기




Volumn 134, Issue 9, 2012, Pages 4037-4040

Total synthesis of (+)-scholarisine A

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ASSIGNMENT OF; INDOLENINE; INTRAMOLECULAR CYCLIZATIONS; LACTONIZATION; REDUCTIVE CYCLIZATION; RING SYSTEMS; TOTAL SYNTHESIS;

EID: 84863229935     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja211840k     Document Type: Article
Times cited : (92)

References (53)
  • 20
    • 84863244401 scopus 로고    scopus 로고
    • note
    • Oxidation state manipulation and/or functionalization would most likely be required for such a fragmentation. Indoline 28, a reported degradation derivative of aspidodasycarpine (see ref 9), possesses the carbon scaffold contained in the akuammiline alkaloids. All members of this class can be considered as oxidized and functionalized analogues of this scaffold. (Chemical Equation Presented)
  • 21
    • 0029057576 scopus 로고
    • Lactone (-)-15 was prepared via the reported four-step enzyme-mediated asymmetrization and functionalization of mesocyclohex-4-ene-1,2-dimethanol. See: (a)
    • Lactone (-)-15 was prepared via the reported four-step enzyme-mediated asymmetrization and functionalization of mesocyclohex-4-ene-1,2-dimethanol. See: (a) Danieli, B.; Lesma, G.; Mauro, M.; Palmisano, G.; Passarella, D. J. Org. Chem. 1995, 60, 2506-2513.
    • (1995) J. Org. Chem. , vol.60 , pp. 2506-2513
    • Danieli, B.1    Lesma, G.2    Mauro, M.3    Palmisano, G.4    Passarella, D.5
  • 23
  • 27
    • 84863239678 scopus 로고    scopus 로고
    • note
    • The structures of (+)-10, (-)-13, (-)-14, (+)-16, (-)-17, (-)-18, (+)-19, (+)-20, and totally synthetic scholarisine A (1) were confirmed by single-crystal X-ray analysis.
  • 31
    • 0001329620 scopus 로고
    • Rhodium on alumina has also been shown to reduce nitriles preferentially to primary amines. See: (b)
    • Rhodium on alumina has also been shown to reduce nitriles preferentially to primary amines. See: (b) Freifelder, M. J. Am. Chem. Soc. 1960, 82, 2386-2389.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 2386-2389
    • Freifelder, M.1
  • 32
    • 8744245263 scopus 로고
    • Bridged azapolycyclic alcohols have been synthesized via intramolecular expoxide opening by an amide. See: (c)
    • Bridged azapolycyclic alcohols have been synthesized via intramolecular expoxide opening by an amide. See: (c) Schultz, R.; Staas, W.; Spurlock, L. J. Org. Chem. 1973, 38, 3091-3093.
    • (1973) J. Org. Chem. , vol.38 , pp. 3091-3093
    • Schultz, R.1    Staas, W.2    Spurlock, L.3
  • 34
    • 0015505219 scopus 로고
    • Our approach to the akuammiline-type alkaloids exploiting a Fischer indole synthesis with the 2-azabicyclo[3.3.1]nonan-8-one ring system was inspired by Dolby's pioneering efforts. See: (a)
    • Our approach to the akuammiline-type alkaloids exploiting a Fischer indole synthesis with the 2-azabicyclo[3.3.1]nonan-8-one ring system was inspired by Dolby's pioneering efforts. See: (a) Dolby, L. J.; Esfandiari, Z. J. Org. Chem. 1972, 37, 43-46.
    • (1972) J. Org. Chem. , vol.37 , pp. 43-46
    • Dolby, L.J.1    Esfandiari, Z.2
  • 36
    • 19944414273 scopus 로고
    • Garg has also recently used this approach (see ref 11). We also note the work of Bosch. See: (c)
    • Garg has also recently used this approach (see ref 11). We also note the work of Bosch. See: (c) Bennasar, M. L.; Zulaica, E.; Lopez, M.; Bosch, J. Tetrahedron Lett. 1988, 29, 2361-2364.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 2361-2364
    • Bennasar, M.L.1    Zulaica, E.2    Lopez, M.3    Bosch, J.4
  • 41
    • 37049102588 scopus 로고
    • Benzoylphenylhydrazine also provided a stable hydrazone intermediate but led to the unprotected indole upon cyclization. See
    • Benzoylphenylhydrazine also provided a stable hydrazone intermediate but led to the unprotected indole upon cyclization. See: Mills, K.; Alkhawaja, K.; Alsaleh, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1981, 636-641.
    • (1981) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 636-641
    • Mills, K.1    Alkhawaja, K.2    Alsaleh, F.3    Joule, J.A.4
  • 53
    • 84863235851 scopus 로고    scopus 로고
    • note
    • The assignment of the absolute configuration of (+)-scholarisine A (1) was derived from the known absolute configurations of (-)-15 and (+)-20.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.