Influence of Diene Substituent Position on the Stereochemical Outcome in IMDA Reaction of Decatrienones. An Asymmetric Synthesis of C10-epi-Dihydro-epi-deoxy Arteannuin B

An asymmetric synthesis of C(10)-epi-dihydro-epi-deoxy arteannuin B is reported employing an IMDA reaction of sugar embedded decatrienone. During this investigation it has been demonstrated that changing the position of the methyl group on the diene moiety changes the stereochemical outcome leading to access to either cis- or trans-decalin derivatives exclusively.