P. Gosselin, A. Perrotin, S. Mille
Jan 21, 2001
Citations
0
Influential Citations
3
Citations
Journal
Tetrahedron
Abstract
Abstract A four-step synthesis of (3aR*,6S*,7aR*)-6,7,7-trimethylhexahydro-2-benzofuran-1(3H)-one 2 has been developed. Lactone 2 is an intermediate in a synthesis of γ-irone. Opening of the Diels–Alder adduct 5 with ethanol afforded hemiester 6b with 87:13 regioselectivity. Subsequent chemoselective reduction of the ester group in 6b yielded hydroxyacid 14 which was lactonized to the cis-fused bicyclic lactone 15. Finally, hydrogenation of 15 into 2 occured with complete diastereoselectivity.