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Paper | Special issue | Vol 50, No. 2, 1999, pp.779-790
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)72
Studies on a Total Synthesis of Plakotenin: Synthesis of Optically Active trans-Hydrindanes by Diastereoselective Asymmetric Intramolecular Diels-Alder Reaction

Miyuki Ishizaki, Yasuhiro Hara, Sachiko Kojima, and Osamu Hoshino*

*Faculty of Pharmaceutical Sciences, Science University of Tokyo, 12, Ichigaya Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan


Diastereoselective asymmetric intramolecular Diels-Alder reaction of 5,5-(trimethylenedithio)-2(E),7(E),9-decatrienoyl amides (13a-e) having various chiral auxiliaries was performed to give optically active trans-hydrindanes, which would be an important intermediate for a total synthesis of plakotenin (1), was described. In the several chiral auxiliaries, Saigo's oxazolidinone was found to give trans-hydrindane (15a) in the highest stereoselectivity (96% e.e.), after conversion to benzyl ester.