Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 71, Issue 7, Pages 2547-2557Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo052314g
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- NIGMS NIH HHS [GM 29098] Funding Source: Medline
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N-Toluenesulfonyl aziridines comprise effective second electrophiles in the solvent controlled three-component linchpin union of silyl dithianes for the stereocontrolled convergent elaboration of protected 1,5-amino alcohols. This tactic, in conjunction with a one-flask sequential cyclization, constitutes an effective general strategy for the construction of indolizidine and related alkaloids, illustrated here with the total syntheses of (-)-indolizidine 223AB (1) and alkaloid (-)-205B (2).
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