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Communication | Special issue | Vol 76, No. 1, 2008, pp.143-154
Published online, 22nd February, 2008
DOI: 10.3987/COM-08-S(N)15
Asymmetric Synthesis of the ABCD Ring System of Daphnilactone B via a Tandem, Double Intramolecular, [4+2] / [3+2]Cycloaddition Strategy

Scott E. Denmark,* Son T. Nguyen, and Ramil Y. Baiazitov

*Department of Chemistry, Roger Adams Laboratory, University of Illinois, Urbana, Illinois 61801, USA


An asymmetric synthesis of the ABCD ring system of daphnilactone B is described. The synthesis features a tandem, double intramolecular, [4+2]/[3+2] cycloaddition of a highly functionalized, enantiomerically enriched nitroalkene to generate a pentacyclic nitroso acetal. The cycloaddition establishes six contiguous stereogenic centers including the critical CD ring junction that bears two quaternary stereogenic centers. Hydrogenolysis of the nitroso acetal followed by amide reduction and cyclization provided the AB rings. The methyl substituent on the A ring was installed in the correct configuration via hydrogenation of an exocyclic olefin in the final step.