1298015-35-6Relevant articles and documents
Phosphate tether-mediated approach to the formal total synthesis of (-)-salicylihalamides A and B
Chegondi, Rambabu,Tan, Mary M. L.,Hanson, Paul R.
, p. 3909 - 3916 (2011/07/08)
A concise formal synthesis of the cytotoxic macrolides (-)- salicylihalamides A and B is reported. Key features of the synthetic strategy include a chemoselective hydroboration, highly regio- and diastereoselective methyl cuprate addition, Pd-catalyzed formate reduction, and an E-selective ring-closing metathesis to construct the 12-membered macrocycle subunit. Overall, two routes have been developed from a readily prepared bicyclic phosphate (4 steps), a 13-step route and a more efficient 9-step sequence relying on regioselective esterification of a key diol.