A concise, selective synthesis of the polyketide spacer domain of a potent bryostatin analogue.
[reaction: see text] A concise, asymmetric synthesis of the polyketide spacer domain portion (C1-C13) of a highly potent bryostatin analogue was developed. The route utilizes asymmetric hydrogenation methodology to install the C3, C5, and C11 stereocenters, while a substrate directed syn reduction sets the C9 stereocenter. The spacer domain 1 is obtained in 10 steps with a 25% overall yield and is readily incorporated into the synthesis of 2.
Wender
Paul A
PA
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. wenderp@leland.stanord.edu
Mayweg
Alexander V W
AV
VanDeusen
Christopher L
CL
D054713:Bryostatins; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D018942:Macrolides; D015394:Molecular Structure
D054713:Bryostatins; D007783:Lactones; D018942:Macrolides; C046785:bryostatin 1