Synthesis of (+)-9a-epi-stemoamide via DBU-catalyzed michael addition of nitroalkane

Synlett

Volumn , Issue 13, 2009, Pages 2188-2190

  Gao, Peng ^a,b   Tong, Zhaolong ^a,d   Hu, Hanwei ^a,e   Xu, Peng Fei ^b   Liu, Wei ^c   Sun, Chunyan ^c   Zhai, Hongbin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b LANZHOU UNIVERSITY   (China)

^c RESEARCH INSTITUTE OF PETROLEUM PROCESSING   (China)

^d GLAXOSMITHKLINE   (China)

^e UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

Michael addition; Nitroalkane; Stemoamide; Synthesis; Unsaturated butyrolactone

Indexed keywords

9A EPISTEMOAMIDE; BUTYROLACTONE; NITROALKANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; MICHAEL ADDITION;

EID: 68949179780     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217558     Document Type: Article

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27. +]: 209.1052; found: 209.1047. Compound 2: To a solution of 6a (22 mg, 0.11 mmol) in anhyd THF (1 mL) at -78°C was added LiHMDS solution in THF (1.0 M, 0.19 mL, 0.19 mmol). After 1 h, MeI (13 μL, 0.21 mmol) was added at -78°C, and the stirring was continued for an additional 1 h.