Total synthesis of echinopines A and B.
Echinopines A and B [(+)-1 and (+)-2], two naturally occurring compounds characterized with a unique [3.5.5.7] carbon framework, have been synthesized in both enantiomeric and racemic forms. Their total synthesis involves a novel intramolecular rhodium-catalyzed cyclopropanation (4 --> 16) and a samarium diiodide-mediated ring closure (3 --> 37).
Nicolaou
K C
KC
Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667. kcn@scripps.edu
Ding
Hanfeng
H
Richard
Jean-Alexandre
JA
Chen
David Y-K
DY
D000447:Aldehydes / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D001688:Biological Products; D004952:Esters; D012717:Sesquiterpenes; C527602:echinopine A; C527604:echinopine B