A short synthetic pathway to a fully-functionalized southern hemisphere of the antitumor macrolide bryostatin 1.
[reaction--see text] An 18-step asymmetric synthesis of the bryostatin 1 "southern hemisphere" fragment (1) has been developed. Key steps include an aldol reaction between 6 and 7 and a dehydration to establish the (E)-exocyclic alkene in 2 and a stereoselective Luche reduction and protection with TESOTf to access 1.
Hale
K J
KJ
The Christopher Ingold Laboratories, The Chemistry Department, University College London, 20 Gordon Street, London WC1H 0AJ, England. k.j.hale@ucl.ac.uk
Frigerio
M
M
Manaviazar
S
S
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D054713:Bryostatins; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D000903:Antibiotics, Antineoplastic; D054713:Bryostatins; D007202:Indicators and Reagents; D007783:Lactones; D018942:Macrolides; C046785:bryostatin 1