Asymmetric synthesis of the northern half C1-C16 of the bryostatins.
Starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one and racemic 2,2-dimethyl-8-oxabicyclo[3.2.1]oct-6-en-3-one, the C1-C16 segment of the bryostatins has been synthesized in 30 steps and 9% overall yield (17 steps longest linear sequence). Fragment coupling by dithiane strategy and protecting group manipulations provided an advanced chemodifferentiated northern half segment.
Vakalopoulos
A
A
Department of Organic Chemistry, University of Hannover, Schneiderberg 1 B, D-30167 Hannover, Germany.
Lampe
T F
TF
Hoffmann
H M
HM
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D054713:Bryostatins; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure
D000970:Antineoplastic Agents; D054713:Bryostatins; D007202:Indicators and Reagents; D007783:Lactones; D018942:Macrolides; C046785:bryostatin 1