publication . Other literature type . 2015

Synthesis of ent-Ketorfanol via a C–H Alkenylation/Highly Torquoselective 6π-Electrocyclization Cascade

Phillips, Eric M.; Mesganaw, Tehetena; Patel, Ashay; Duttwyler, Simon; Mercado, Brandon Q.; Houk, Kendall N.; Ellman, Jonathan A.;
Open Access English
  • Published: 17 Aug 2015
Abstract
The asymmetric synthesis of ent-ketorfanol from simple and commercially available precursors is reported. A Rh(I)-catalyzed intramolecular C–H alkenylation/highly torquoselective 6π-electrocyclization cascade provides a fused bicyclic 1,2-dihydropyridine as a key intermediate. Computational studies were performed to understand the high torquoselectivity of the key 6π electrocyclization. Computations demonstrate a conformational effect is responsible for the observed selectivity. The ketone functionality and final ring are introduced in a single step by a redox neutral acid-catalyzed rearrangement of a vicinal diol to the requisite carbonyl followed by intramolec...
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Other literature type . 2015
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