1429226-35-6Relevant articles and documents
An asymmetric synthesis of the pentacyclic core of stemofoline
Burns, Thomas,Helliwell, Madeleine,Thomas, Eric J.
, p. 2120 - 2123 (2013/05/09)
On treatment with acid, an open-chain 5-acylamino-3,8-diketo-ester, methyl (4R,5S,7S)-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, (4R,5R,8S,9R,10S,12S,13S)-13-butyl-8-methyl-1-aza-6,14-dioxapentacyclo[8.3.0. 04,1305,9.15,12]tetradecan-2-one, that corresponds to the pentacyclic core of stemofoline.