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Volumn 12, Issue 24, 2010, Pages 5704-5707

Concise synthesis of the erythrina alkaloid 3-demethoxyerythratidinone via combined rhodium catalysis

Author keywords

[No Author keywords available]

Indexed keywords

3 DEMETHOXYERYTHRATIDINONE; 3-DEMETHOXYERYTHRATIDINONE; INDOLE ALKALOID; RHODIUM;

EID: 78650340889     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102535u     Document Type: Article
Times cited : (31)

References (41)
  • 2
    • 77956830705 scopus 로고    scopus 로고
    • Ed; Academic Press: New York
    • Sano, T. and Tsuda, Y. In The Alkaloids; Cordell, G. A., Ed; Academic Press: New York, 1996; Vol. 48, pp 249 - 337.
    • (1996) The Alkaloids , vol.48 , pp. 249-337
    • Sano, T.1    Tsuda, Y.2    Cordell, G.A.3
  • 3
    • 33847722224 scopus 로고    scopus 로고
    • Synthesis Pathways to Erythrina Alkaloids and Erythrina Type Compounds
    • Herz, W., Falk, H., and Kirby, G. W., Eds.; Springer-Verlag/Wien: Austria
    • For a recent review on the synthesis of erythrina alkaloids, see Reimann, E. Synthesis Pathways to Erythrina Alkaloids and Erythrina Type Compounds. In Progress in the chemistry of organic natural products; Herz, W., Falk, H., and Kirby, G. W., Eds.; Springer-Verlag/Wien: Austria, 2007; Vol. 88, pp 1 - 62.
    • (2007) Progress in the Chemistry of Organic Natural Products , vol.88 , pp. 1-62
    • Reimann, E.1
  • 10
    • 78650394552 scopus 로고    scopus 로고
    • For reports on the total synthesis of 3-demethoxyerythratidinone, see
    • For reports on the total synthesis of 3-demethoxyerythratidinone, see
  • 23
    • 78650358093 scopus 로고    scopus 로고
    • For reports on the formal synthesis, see
    • For reports on the formal synthesis, see
  • 30
    • 78650355341 scopus 로고    scopus 로고
    • Portions of this work are taken from preliminary studies: Ph.D. Dissertation, Princeton University, NJ
    • Portions of this work are taken from preliminary studies: Joo, J. M. Ph.D. Dissertation, Princeton University, NJ, October 2008.
    • (2008)
    • Joo, J.M.1
  • 31
    • 78650357445 scopus 로고    scopus 로고
    • A.B. Dissertation, Princeton University, NJ
    • David, R. A. A.B. Dissertation, Princeton University, NJ, June 2008.
    • (2008)
    • David, R.A.1
  • 33
    • 78650326941 scopus 로고    scopus 로고
    • For a similar sequence to prepare a dihydroisoquinoline, see
    • For a similar sequence to prepare a dihydroisoquinoline, see
  • 35
  • 36
    • 78650402590 scopus 로고    scopus 로고
    • Interestingly, the reaction employing 1,2-diiodoethane did not result in a similar N -alkylation, but instead led to iodinium-induced cyclization of the alkenylimine to give an iodoiminium salt. See Supporting Information
    • Interestingly, the reaction employing 1,2-diiodoethane did not result in a similar N -alkylation, but instead led to iodinium-induced cyclization of the alkenylimine to give an iodoiminium salt. See Supporting Information.
  • 37
    • 34250891949 scopus 로고    scopus 로고
    • For a review on addition reactions of N, O -acetals, see:;, For selected examples of the addition of alkynyl Grignard reagents to N, O -acetals, see:; Angew. Chem., Int. Ed. 2007, 46, 2631
    • For a review on addition reactions of N, O -acetals, see: Yamazaki, N.; Kibayashi, C. J. Synth. Org. Chem. Jpn. 2003, 61, 38 For selected examples of the addition of alkynyl Grignard reagents to N, O -acetals, see: Caldwell, J. J.; Craig, D. Angew. Chem., Int. Ed. 2007, 46, 2631
    • (2003) J. Synth. Org. Chem. Jpn. , vol.61 , pp. 38
    • Yamazaki, N.1    Kibayashi, C.2    Caldwell, J.J.3    Craig, D.4
  • 40
    • 78650326413 scopus 로고    scopus 로고
    • Resubjection of 16 to the rhodium-catalyzed tandem cyclization conditions resulted only in the recovery of the starting material
    • Resubjection of 16 to the rhodium-catalyzed tandem cyclization conditions resulted only in the recovery of the starting material.
  • 41
    • 78650408282 scopus 로고    scopus 로고
    • See Supporting Information for the detailed results of the base screening experiments
    • See Supporting Information for the detailed results of the base screening experiments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.