title: Direct entry to erythronolides via a cyclic bis[allene].
abstract: The complexity and low tractability of antibiotic macrolides pose serious challenges to addressing the problem of resistance through semi- or total synthesis. Here we describe a new strategy involving the preparation of a complex yet tractable macrocycle and the transformation of this macrocycle into a range of erythronolide congeners. These compounds represent valuable sectors of erythromycinoid structure space and constitute intermediates with the potential to provide further purchase in this space. The routes are short. The erythronolides were prepared in three or fewer steps from the macrocycle, which was prepared in a longest linear sequence of 11 steps.
authors: Department of Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey 08854, United States.
authors: Kai
authors: K
authors: Liu
authors: Hiyun
authors: H
authors: Kim
authors: Partha
authors: P
authors: Ghosh
authors: Novruz G
authors: NG
authors: Akhmedov
authors: Lawrence J
authors: LJ
authors: Williams
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D004917:Erythromycin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D004917:Erythromycin