Enantioselective total synthesis of (+)-conicol via cascade three-component organocatalysis.
The first asymmetric total synthesis of (+)-conicol has been achieved via a key step reaction involving the organocatalytic domino oxa-Michael-Michael-Michael-aldol condensation of 2-((E)-2-nitrovinyl)benzene-1,4-diol and alpha,beta-unsaturated aldehydes. Structures of the three-component domino reaction adducts, 20 and 21, including their absolute configurations, were confirmed unambiguously by X-ray analysis. Through this work, the absolute configuration of (+)-conicol was thereby elucidated.
Hong
Bor-Cherng
BC
Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621, Taiwan, ROC. chebch@ccu.edu.tw
Kotame
Prakash
P
Tsai
Chih-Wei
CW
Liao
Ju-Hsiou
JH
D000447:Aldehydes / Q000737:chemistry; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D000882:Haplorhini; D006801:Humans; D008386:Marine Biology; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014561:Urochordata / Q000737:chemistry
D000447:Aldehydes; D000970:Antineoplastic Agents; D013729:Terpenes; C547631:conicol