New, abridged pathway to Masamune's "southern hemisphere" intermediate for the total synthesis of bryostatin 7.
[reaction: see text] The "Southern Hemisphere" intermediate 2, used by Masamune and co-workers for their asymmetric total synthesis of bryostatin 7 (1), has been synthesized from (E)-1,4-hexadiene (11) by a 24-step pathway that has a longest linear sequence of only 20 steps. This is the shortest synthesis of 2 so far recorded, and moreover, it is fully stereocontrolled.
Hale
Karl J
KJ
The Christopher Ingold Laboratories, The Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, United Kingdom. k.j.hale@ucl.ac.uk
Frigerio
Mark
M
Manaviazar
Soraya
S
D000475:Alkenes; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D054713:Bryostatins; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D009942:Organometallic Compounds
D000475:Alkenes; D000970:Antineoplastic Agents; D054713:Bryostatins; D007783:Lactones; D018942:Macrolides; D009942:Organometallic Compounds; C475531:bryostatin 7; C046771:butyllithium; C046785:bryostatin 1