Intramolecular Diels-Alder/Tsuji allylation assembly of the functionalized trans-decalin of salvinorin A.
An enantioselective synthesis of the highly functionalized trans-decalin core (2) of salvinorin A is described. The tetraene 4 was synthesized in six steps from a known L-(+)-tartaric acid derivative. Three contiguous stereocenters, two of them quaternary, on the trans-decalin were established asymmetrically by an intramolecular Diels-Alder/Tsuji allylation sequence.
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Aaron C
AC
Burns
Craig J
CJ
Forsyth
D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D045785:Diterpenes, Clerodane; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
D004224:Diterpenes; D045785:Diterpenes, Clerodane; D009281:Naphthalenes; C007229:decalin; C090499:salvinorin A