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Volumn 9, Issue 7, 2007, Pages 1275-1278

Highly stereoselective [4 + 3] cycloadditions of nitrogen-stabilized oxyallyl cations with pyrroles. An approach to parvineostemonine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALLYL COMPOUND; BRIDGED COMPOUND; CATION; NITROGEN; PARVINEOSTEMONINE; PYRROLE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

EID: 34147154096     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070103n     Document Type: Article
Times cited : (69)

References (72)
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    • (b) For our preliminary communication, see: Abstracts of Papers, 231st ACS National Meeting of the American Chemical Society, Atlanta, GA, Spring 2006; American Chemical Society: Washington, DC, 2006; Abstract No. ORON192. During our efforts, MaGee and Walters reported one example of pyrrole-[4 + 3] cycloaddition employing nitrogen-stabilized oxyallyl cations derived from, α-bromo-α-amido ketones, although the yield was low [see ref 3a].
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    • Acidic conditions used to remove the Boc group led to pyrrole li via a retro-Mannich fragmentation followed by re-aromatization of the iminium intermediate i. This in essence represents an equivalent of the Type III cycloadduct or a-arylation of a methyl ketone. For a recent elegant account related to this fragmentation, see: Cramer, N, Juretschke, J, Laschat, S, Baro, A, Frey, W, Chem. 2004, 1397. Figure presented
    • Acidic conditions used to remove the Boc group led to pyrrole li via a retro-Mannich fragmentation followed by re-aromatization of the iminium intermediate i. This in essence represents an equivalent of the Type III cycloadduct or a-arylation of a methyl ketone. For a recent elegant account related to this fragmentation, see: Cramer, N.; Juretschke, J.; Laschat, S.; Baro, A.; Frey, W. Eur. J. Org. Chem. 2004, 1397. Figure presented.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.