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Volumn 62, Issue 3, 1997, Pages 440-441

Aloperine: Stereocontrolled synthesis of two stereoisomers and determination of absolute configuration

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALOPERINE; UNCLASSIFIED DRUG;

EID: 0031017255     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9621231     Document Type: Article
Times cited : (35)

References (40)
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    • For recent studies of the participation of nucleophiles in Mannich cyclizations of alkynes, see, inter alia: (a) Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 1988, 110, 612. (b) Lin, N.-H.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9062. (c) Caderas, C.; Lett, R.; Overman, L. E.; Rabinowitz, M. H.; Robinson, L. A.; Sharp, M. J.; Zablocki, J. J. Am. Chem. Soc. 1996, 118, 9073.
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    • TsCl, pyridine, rt
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    • 3, 18-crown-6, benzene, reflux
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    • 4, HCl, EtOH, -12°C
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    • No isomers of 9 were detected in the crude cyclization product; however, trace amounts of the tricyclic alkene that is formed upon treatment of 9 with DBU were seen
    • No isomers of 9 were detected in the crude cyclization product; however, trace amounts of the tricyclic alkene that is formed upon treatment of 9 with DBU were seen.
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    • To our knowledge, this transformation is the first example of coupling an α-iodo enone with a nitrogen-containing borane partner. For related precedents, see: (a) Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014. (b) Narukawa, Y.; Nishi, K.; Onoue, H. Tetrahedron Lett. 1996, 37, 2589.
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    • To our knowledge, this transformation is the first example of coupling an α-iodo enone with a nitrogen-containing borane partner. For related precedents, see: (a) Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014. (b) Narukawa, Y.; Nishi, K.; Onoue, H. Tetrahedron Lett. 1996, 37, 2589.
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    • note
    • 13C NMR analyses.
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    • 11, respectively, with respect to the methano bridge
    • 11, respectively, with respect to the methano bridge.
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    • 25
    • 25
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    • note
    • The authors have deposited atomic coordinates for 2 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.