139. Enantioselective synthesis and absolute configuration of (–)-pulo'upone by asymmetric intramolecular diels-alder reaction
     Oppolzer, W.; Dupuis, D.; Poli, G.; Raynham, T. M.; Bernardinelli, G.
     Tetrahedron Lett. 1988, 29, 5885-5888

(−)-Pulo'upone (1) was synthesized via an asymmetric, bornane-10,2-sultam- directed, intramolecular Diels- Alder reaction (3 → 2) and a 2-pyridylcuprate/allylacetate coupling (18 → 1). The (6'R, 9'S, 13'R, 14'R)- configuration of (−)-1 follows from an X-ray diffraction analysis of the cycloaddition product 2.

DOI : 10.1016/S0040-4039(00)82216-9 

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