Total synthesis and stereochemical assignment of (±)-sorbiterrin A.
Porco, John A.
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CitationChao Qi, Tian Qin, Daisuke Suzuki, John A Porco. 2014. "Total synthesis and stereochemical assignment of (±)-sorbiterrin A.." J Am Chem Soc, Volume 136, Issue 9, pp. 3374 - 3377.
A concise, biomimetic approach to sorbiterrin A has been developed employing consecutive Michael additions of a 4-hydroxypyrone to a sorbicillinol derivative and silver nanoparticle-mediated bridged aldol/dehydration to construct the [3.3.1] ring system. The relative stereochemistry of sorbiterrin A was unambiguously confirmed by X-ray crystallographic analysis.