Symmetry-driven synthesis of 9-demethyl-10,15-dideoxyryanodol

Abstract

Ryanodine, a potent modulator of calcium release channels, possesses a highly oxygenated multicyclic structure. To develop a new unified strategy for the construction of ryanodine and its derivatives, we designed 9-demethyl-10,15-dideoxyryanodol (1) as a model compound. Here we report an efficient synthesis of 1 with seven contiguous tetrasubstituted carbons by taking advantage of the C₂-symmetric substructure embedded within its main structure.