期刊
ORGANIC LETTERS
卷 3, 期 24, 页码 3923-3925出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol016795b
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资金
- NIGMS NIH HHS [GM 28553] Funding Source: Medline
[GRAPHICS] Intramolecular electrophilic aromatic substitution reactions of 2-amidoacroleins constitute the key steps in the total syntheses of lennoxamine and aphanorphine. The aldehyde moiety of one cyclization product was transformed to a double bond, which was then engaged in a radical cyclization to produce the complete ring system of lennoxamine. The aldehyde functionality of the other cyclization product was converted to the corresponding mesylate, which underwent intramolecular displacement by a lactam enolate to furnish the ring system of aphanorphine.
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