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Short Paper | Special issue | Vol 93, No. 2, 2016, pp.783-791
Published online, 29th September, 2015
DOI: 10.3987/COM-15-S(T)34
Construction of cis-Fused Hydrindane Skeleton with a Lactone Tether Utilizing Intramolecular Diels-Alder Reaction

Shuqiang Yin, Kenji Takai, Daishiro Minato, Kenji Sugimoto, Hideki Ohtsu, Kiyoshi Tsuge, and Yuji Matsuya*

*Graduate School of Medicine and Pharmaceutical Sciences for Research, University of Toyama, Sugitani 2630, Toyama, 930-0194, Japan


Synthetically important, cis-fused hydrindane skeleton having quaternary angular stereogenic centers was selectively furnished by intramolecular Diels-Alder reaction of ester-tethered precursor via endo transition state. The reaction was applicable for a construction of the steroidal BCD ring system with cis-hydrindane framework.