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Volumn 5, Issue 1, 2014, Pages 333-340

Application of diazene-directed fragment assembly to the total synthesis and stereochemical assignment of (+)-desmethyl-meso-chimonanthine and related heterodimeric alkaloids

Author keywords

[No Author keywords available]

Indexed keywords

CONTROLLED SYNTHESIS; DIAZENES; DIRECTED ASSEMBLY; ENANTIOSELECTIVE TOTAL SYNTHESIS; FRAGMENT ASSEMBLY; HETERODIMERIZATION; HIGHER ORDER DERIVATIVES; TOTAL SYNTHESIS;

EID: 84888633858     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc52451e     Document Type: Article
Times cited : (67)

References (138)
  • 1
    • 0542403141 scopus 로고
    • in, ed. R. H. F. Manske and R. G. A. Rodrigo, Academic Press, New York, 3-294
    • G. A. Cordell and J. E Saxton, in The Alkaloids: Chemistry and Physiology, ed., R. H. F. Manske, and, R. G. A. Rodrigo, Academic Press, New York, 1981, vol. 20, pp. 3-294
    • (1981) The Alkaloids: Chemistry and Physiology , vol.20
    • Cordell, G.A.1    Saxton J, E.2
  • 124
    • 79959661268 scopus 로고    scopus 로고
    • See the ESI for details. In the intramolecular Rh-catalyzed C-H amination, secondary ethereal C-H bonds react preferentially over both secondary benzylic and tertiary C-H bonds, see ref. 19g tert-Butylbenzenesulfonyl protective group was utilized to increase solubility of tricycle (-)- 18 in isopropyl acetate, the optimal solvent for the rhodium-catalyzed C-H amination For key references on oxidation of sulfamides, see
    • B. M. Trost B. M. O'Boyle W. Torres M. K. Ameriks Chem.-Eur. J. 2011 17 7890
    • (2011) Chem.-Eur. J. , vol.17 , pp. 7890
    • Trost, B.M.1    O'Boyle, B.M.2    Torres, W.3    Ameriks, M.K.4
  • 136
    • 33846310576 scopus 로고
    • The acid-mediated rearrangement of meso-chimonanthine under similar conditions has previously been described by Overman and co-workers, see: ref. 4i. For the acid mediated rearrangement of a related natural product containing the meso-chimonanthine substructure, see
    • R. G. Eccles Proc. Assoc. Am. Physicians 1888 84 382
    • (1888) Proc. Assoc. Am. Physicians , vol.84 , pp. 382
    • Eccles, R.G.1
  • 138
    • 0037036807 scopus 로고    scopus 로고
    • Although the specific decomposition products could not be fully identified, mass spectral analysis indicated the presence of oxindole related byproducts Attempts at the acid-mediated rearrangement of both (-)-calycanthidine (1) and (+)-DMMC (3) led to exclusive fragmentation of the C3a-C3a′ bond as evidenced by the isolation of N-methyltryptamine. A similar result has been observed in the attempted acid-mediated rearrangement of (±)-folicanthine, see ref. 4h
    • A. D. Lebsack J. T. Link L. E. Overman B. A. Sterns J. Am. Chem. Soc. 2002 124 9008
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 9008
    • Lebsack, A.D.1    Link, J.T.2    Overman, L.E.3    Sterns, B.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.