TESOTf-induced rearrangement of quinols. Efficient construction of the fully functionalized carbon skeleton of the griseusins by a divergent-reconvergent approach.
[reaction: see text] The "reverse polarity" or "umpolung" strategy for the total synthesis of aryl C-glycosides was developed in the context of the antibiotic (-)-griseusin B. Although a key reaction in a model sequence for the total synthesis produced two structurally divergent products, both were converted to the same advanced model intermediate that contains the complete carbon skeleton and (except for the extraneous oxygen substituent in the model series) the functional group pattern of the griseusins.
Parker
Kathlyn A
KA
Department of Chemistry, SUNY Stony Brook, Stony Brook, New York 11794-3400, USA. kparker@notes.cc.sunysb.edu
Mindt
Thomas L
TL
Koh
Yung-hyo
YH
D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006873:Hydroquinones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D006027:Glycosides; D006873:Hydroquinones; D009285:Naphthoquinones; C012339:griseusin