Thomas Burns, M. Helliwell, E. Thomas
Apr 1, 2013
Citations
0
Influential Citations
9
Citations
Journal
Tetrahedron Letters
Abstract
Abstract On treatment with acid, an open-chain 5-acylamino-3,8-diketo-ester, methyl (4 R ,5 S ,7 S )-7-benzyloxy-4-[( S )-1-benzyloxyprop-2-yl]-5-methoxycarbonylamino-3,8-dioxododecanoate, cyclised via a stereoselective Mannich reaction to give an 8-azabicyclo[3.2.1]octanone. Hydrogenolysis of this with in situ acetal formation, reduction of the ester and a further cyclisation gave a lactam, (4 R ,5 R ,8 S ,9 R ,10 S ,12 S ,13 S )-13-butyl-8-methyl-1-aza-6,14-dioxapentacyclo[8.3.0.0 4,13 0 5,9 .1 5,12 ]tetradecan-2-one, that corresponds to the pentacyclic core of stemofoline.