Synthesis of the fully glycosylated cyclohexenone core of lomaiviticin A.
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.
Gholap
Shivajirao L
SL
Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.
Woo
Christina M
CM
Ravikumar
P C
PC
Herzon
Seth B
SB
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
D003512:Cyclohexanones; D005449:Fluorenes; C433842:lomaiviticin A; D000095602:Angucyclines and Angucyclinones