title: Synthesis of the fully glycosylated cyclohexenone core of lomaiviticin A.
abstract: We describe two four-step sequences for conversion of the inexpensive reagent ethyl sorbate to either O-allyl-N,N-dimethyl-D-pyrrolosamine or O-allyl-L-oleandrose, protected forms of the 2,6-dideoxy sugar residues found in the complex bacterial metabolite lomaiviticin A. We also report a gram-scale synthesis of the highly-oxygenated cyclohexenone ring of this metabolite, and show this may be coupled with the aforementioned donors to form the bis(glycoside) 6. The longest linear sequence to 6 is nine steps.
authors.affiliation: Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.
authors.forename: Shivajirao L
authors.initials: SL
authors.lastname: Gholap
authors.forename: Christina M
authors.initials: CM
authors.lastname: Woo
authors.forename: P C
authors.initials: PC
authors.lastname: Ravikumar
authors.forename: Seth B
authors.initials: SB
authors.lastname: Herzon
mesh_terms: D003512:Cyclohexanones / Q000138:chemical synthesis* / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism; D000095602:Angucyclines and Angucyclinones
chemical_list: D003512:Cyclohexanones; D005449:Fluorenes; C433842:lomaiviticin A; D000095602:Angucyclines and Angucyclinones