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Volumn , Issue 5, 2007, Pages 504-506

Asymmetric total synthesis of martinelline and martinellic acid

Author keywords

[No Author keywords available]

Indexed keywords

MARTINELLIC ACID; MARTINELLINE; PLANT EXTRACT; UNCLASSIFIED DRUG;

EID: 33846553001     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b611121a     Document Type: Article
Times cited : (72)

References (47)
  • 29
    • 0037121605 scopus 로고    scopus 로고
    • Formal synthesis of (-)-martinellic acid and martinelline:
    • C. Xia L. Heng D. Ma Tetrahedron Lett. 2002 43 9405 9409
    • (2002) Tetrahedron Lett. , vol.43 , pp. 9405-9409
    • Xia, C.1    Heng, L.2    Ma, D.3
  • 36
    • 33846501054 scopus 로고    scopus 로고
    • Although Aubé's group attempted various treatments, including the use of heat, acids, electrophiles and bases to generate an ortho-azaxylylene, they obtained no Diels-Alder adducts For a review on recent developments in imino Diels-Alder eactions, see:
    • Although Aubé's group attempted various treatments, including the use of heat, acids, electrophiles and bases to generate an ortho-azaxylylene, they obtained no Diels-Alder adducts
  • 39
    • 0035801853 scopus 로고    scopus 로고
    • 1H NMR signal of the carbamate hydrogen (7 and 10) shifts significantly downfield (ca. 12.4-12.5 ppm). Therefore, we believe that the mechanism of the Mukaiyama-Mannich reaction is via an indirect activation route rather than a direct one Detailed procedures for the preparation of 10, 11 and 12 are available in the ESI.
    • J. S. Yadav B. V. S. Reddy C. R. Madhuri G. Sabitha B. Jaganadh S. Kumar Tetrahedron Lett. 2001 42 6381 6384
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6381-6384
    • Yadav, J.S.1    Reddy, B.V.S.2    Madhuri, C.R.3    Sabitha, G.4    Jaganadh, B.5    Kumar, S.6
  • 42
    • 0034625424 scopus 로고    scopus 로고
    • The complexation of a Lewis acid to the nitrogen atom of pyrrolidine would lead to the deactivation and inhibition of acyliminium ion formation
    • W. N. Speckamp M. J. Moolenaar Tetrahedron 2000 56 3817 3856
    • (2000) Tetrahedron , vol.56 , pp. 3817-3856
    • Speckamp, W.N.1    Moolenaar, M.J.2
  • 47
    • 0034615897 scopus 로고    scopus 로고
    • The detailed procedures for the conversion of 13b to (+)- 1 and 2 are available in the ESI We know that, in the absence of a direct comparison with a natural product, we cannot conclude with certainty that the natural Martinella alkaloids are racemic, because there might be several factors associated with the difference in optical rotation; for example, purity, the degree of protonation and the state of aggregation It is interesting to note Batey's insightful proposal 4d that Martinella alkaloids are conceivably biosynthesized through an unprecedented enzyme-catalyzed Povarov-type intermolecular h-DA reaction between an aniline-derived imine and an endocyclic enamine.
    • C. M. Zeng M. Han D. F. Covey J. Org. Chem. 2000 65 2264 2266
    • (2000) J. Org. Chem. , vol.65 , pp. 2264-2266
    • Zeng, C.M.1    Han, M.2    Covey, D.F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.