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2004
Terpenes
U 0200
44- 206
Highly Efficient Transfer of Chirality from Macrocyclic Conformation in the
Tandem Oxy-Cope/Claisen/Ene Reaction. — The title reaction is a powerful and
simple method to produce the decalin framework of neo-clerodane and pimarane diterpenes. The tandem reaction is triggered by an oxy-Cope rearrangement to create in
situ a 10-membered ring enol ether macrocycle, which immediately rearranges via a
Claisen [3,3] shift followed by spontaneous cyclization via a transannular ene reaction.
— (SAUER, E. L. O.; BARRIAULT*, L.; J. Am. Chem. Soc. 126 (2004) 27,
8569-8575; Dep. Chem., Univ. Ottawa, Ottawa, Ont. K1N 6N5, Can.; Eng.) —
S. Adam
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