메뉴 건너뛰기




Volumn 46, Issue 20, 2007, Pages 3725-3728

Concise total synthesis of (-)-calycanthine, (+)-chimonanthine, and (+)-folicanthine

Author keywords

Alkaloids; Dimerization; Enantioselectivity; Indoles; Total synthesis

Indexed keywords

ALKALOIDS; INDOLES; STEREOCENTERS; TOTAL SYNTHESIS;

EID: 34250811388     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700705     Document Type: Article
Times cited : (241)

References (43)
  • 1
    • 85013528497 scopus 로고    scopus 로고
    • Bisindole Alkaloids: G. A. Cordell, J. E. Saxton in The Alkaloids: Chemistry and Physiology, 20, (Eds.: R. H. F. Manske, R. G. A. Rodrigo), Academic Press, New York, 1981, pp. 3-294;
    • a) "Bisindole Alkaloids": G. A. Cordell, J. E. Saxton in The Alkaloids: Chemistry and Physiology, Vol. 20, (Eds.: R. H. F. Manske, R. G. A. Rodrigo), Academic Press, New York, 1981, pp. 3-294;
  • 2
    • 0043288716 scopus 로고    scopus 로고
    • Chemistry and Reactions of Cyclic Tautomers of Tryptamines and Tryptophans: T. Hino, M. Nakagawa in The Alkaloids: Chemistry and Pharmacology, 34 (Ed.: A. Brossi), Academic Press, New York, 1989, pp. 1-75;
    • b) "Chemistry and Reactions of Cyclic Tautomers of Tryptamines and Tryptophans": T. Hino, M. Nakagawa in The Alkaloids: Chemistry and Pharmacology, Vol. 34 (Ed.: A. Brossi), Academic Press, New York, 1989, pp. 1-75;
  • 3
    • 34250900742 scopus 로고    scopus 로고
    • Alkaloids from the Medicinal Plants of New Caledonia: T. Sévenet, J. Pusset in The Alkaloids: Chemistry and Pharmacology, 48 (Ed.: G. A. Cordell), Academic Press, New York, 1996, pp. 58-59;
    • c) "Alkaloids from the Medicinal Plants of New Caledonia": T. Sévenet, J. Pusset in The Alkaloids: Chemistry and Pharmacology, Vol. 48 (Ed.: G. A. Cordell), Academic Press, New York, 1996, pp. 58-59;
  • 19
  • 20
    • 0033616097 scopus 로고    scopus 로고
    • For an important precedent on the isolation (10-15%) of a dimeric by-product during prenylation studies at the C3a-position of an exo-hexahydropyrroloindole-derived selenide directed towards amauromine, see: K. M. Depew, S. P. Marsden, D. Zatorska, A. Zatorski, W. G. Bornmann, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 11953.
    • For an important precedent on the isolation (10-15%) of a dimeric by-product during prenylation studies at the C3a-position of an exo-hexahydropyrroloindole-derived selenide directed towards amauromine, see: K. M. Depew, S. P. Marsden, D. Zatorska, A. Zatorski, W. G. Bornmann, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 11953.
  • 26
    • 34250792543 scopus 로고    scopus 로고
    • For details, please see the Supporting Information
    • For details, please see the Supporting Information.
  • 29
    • 34250861827 scopus 로고    scopus 로고
    • We attribute the greater stability of, -9 toward acids in part to attenuation of the Lewis basicity of the carbamate at Nα by the ester at the C2-position
    • α by the ester at the C2-position.
  • 31
    • 34250834147 scopus 로고    scopus 로고
    • As a result of the slow conformational equilibration at ambient temperature, NMR spectra in this report were collected at 50-100°C.
    • As a result of the slow conformational equilibration at ambient temperature, NMR spectra in this report were collected at 50-100°C.
  • 35
    • 34250892295 scopus 로고    scopus 로고
    • A minor competing pathway is the disproportionation of 13 as suggested by the isolation of 9 (10%) from the dimerization reaction.
    • A minor competing pathway is the disproportionation of 13 as suggested by the isolation of 9 (10%) from the dimerization reaction.
  • 36
    • 34250891098 scopus 로고    scopus 로고
    • While we have no experimental evidence for this hypothesis at this time, we expect such cobalt(III) complexes to contain a labile C-Co bond; mechanistic studies are planned to investigate this hypothesis
    • While we have no experimental evidence for this hypothesis at this time, we expect such cobalt(III) complexes to contain a labile C-Co bond; mechanistic studies are planned to investigate this hypothesis.
  • 43
    • 34250876073 scopus 로고    scopus 로고
    • The sign of optical rotation and the absolute stereochemistry for (+)-2 conform with revision of the absolute stereochemistry of (-)- and (+)-chimonanthine (1) by Overman et al.; see Ref. [4b-c].
    • The sign of optical rotation and the absolute stereochemistry for (+)-2 conform with revision of the absolute stereochemistry of (-)- and (+)-chimonanthine (1) by Overman et al.; see Ref. [4b-c].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.