Enantioselective formal total synthesis of the antitumor macrolide bryostatin 7.
A new enantioselective synthesis of Masamune's AB fragment (1) for bryostatin 7 is described. Key steps in the new route include a Meerwein-Ponndorf-Verley reduction to set the O(7) stereocenter and an alkylative union between the dithiane 6 and iodide 5 to construct the C(9)-C(10) bond. Because we have previously published a synthesis of Masamune's C-ring phenyl sulfone 2, our new route to 1 constitutes a formal total synthesis of bryostatin 7; it also corrects the previously reported spectral data for 1 in CDCl3.
Manaviazar
Soraya
S
UCL Center for Chemical Genomics, Christopher Ingold Laboratories, Chemistry Department, University College London, 20 Gordon Street, London WC1H 0AJ, UK. s.manaviazar@ucl.ac.uk
Frigerio
Mark
M
Bhatia
Gurpreet S
GS
Hummersone
Marc G
MG
Aliev
Abil E
AE
Hale
Karl J
KJ
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D054713:Bryostatins; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D054713:Bryostatins; D018942:Macrolides; C475531:bryostatin 7