Synthesis of the bis(cyclohexenone) core of (-)-lomaiviticin A.

ABSTRACT: (-)-Lomaiviticin A is a complex C ₂-symmetric bacterial metabolite comprising two diazotetrahydrobenzo[b]fluorene (diazofluorene) residues and four 2,6-dideoxy glycosides, α-l-oleandrose and N,N-dimethyl-β-l-pyrrolosamine. The two halves of lomaiviticin A are linked by a single carbon-carbon bond oriented syn with respect to the oleandrose residues. While many advances toward the synthesis of lomaiviticin A have been reported, including synthesis of the aglycon, a route to the bis(cyclohexenone) core bearing any of the carbohydrate residues has not been disclosed. Here we describe a short route to a core structure of lomaiviticin A bearing two α-l-oleandrose residues. The synthetic route features a Stille coupling to form the conjoining carbon-

SUBMITTER: Rose JA 

PROVIDER: S-EPMC8159427 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature