Total synthesis of (-)-xyloketal A.
[reaction: see text] The first total synthesis of the C(3)-symmetric and biologically active natural product, (-)-xyloketal A, has been accomplished in one step from phloroglucinol (1,3,5-trihydroxybenzene) and (4R)-3-hydroxymethyl-2,4-dimethyl-4,5-dihydrofuran. This remarkably direct process involved an exceedingly facile and diastereoselective boron trifluoride diethyl etherate-promoted triple electrophilic aromatic substitution reaction that was coupled to three bicyclic acetal formation reactions.
Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia V5A 1S6, Canada.
Jeremy D
JD
Pettigrew
Peter D
PD
Wilson
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013098:Xylariales / Q000737:chemistry
D001688:Biological Products; D011714:Pyrans; C438053:xyloketal A