The first total synthesis of (+)-tricycloclavulone having a unique tricyclo[5,3,0,01,4]decane skeleton and six chiral centers was achieved in a highly stereoselective manner. It includes a catalytic enantioselective [2+2]-cycloaddition reaction using novel chiral copper catalyst, extremely effecting an intramolecular ester transfer reaction, and asymmetric reduction of the carbonyl group on the alpha-chain using Noyori's chiral ruthenium catalyst.
Cyclopentane derivatives Q 0030Catalytic Enantioselective [2 + 2]-Cycloaddition Reaction of 2-Methoxycarbonyl-2-cyclopenten-1-one by Chiral Copper Catalyst. -It is found that the cyclopentenone (I) can undergo enantioselective [2 + 2]-cycloaddition with thioacetylenes in the presence of (R)-and (S)-PBN. The cycloadduct (III) is a useful precursor of the marine prostanoid tricycloclavulone. -(TAKENAKA, Y.; ITO*, H.; HASEGAWA, M.; IGUCHI, K.; Tetrahedron 62 (2006) 14, 3380-3388; Sch. Life Sci., Univ. Pharm. Life Sci., Hachioji, Tokyo 192, Japan; Eng.) -Jannicke 30-068
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