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.
Pettigrew
Jeremy D
JD
Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia V5A 1S6, Canada.
Wilson
Peter D
PD
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