A modular phosphate tether-mediated divergent strategy to complex polyols

Abstract

SummaryAn efficient and divergent synthesis of polyol subunits utilizing a phosphate tether-mediated, one-pot, sequential RCM/CM/reduction process is reported. A modular, 3-component coupling strategy has been developed, in which, simple “order of addition” of a pair of olefinic-alcohol components to a pseudo-C 2-symmetric phosphoryl chloride, coupled with the RCM/CM/reduction protocol, yields five polyol fragments. Each of the product polyols bears a central 1,3-anti-diol subunit with differential olefinic geometries at the periphery.

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

“…296) was employed in the synthesis of complex polyol derivatives (e.g. [740]. Numerous macrocyclic compounds (rings with ≥ 11 atoms) were synthesized using the RCM reaction in 2014 ( Figure 13), including: (1) a macrocyclic hydrocarbon symmetrically fused to two quinolizidine rings (e.g.…”

A Pot-Economical Approach to the Total Synthesis of Sch-725674

“…Previous reports in our group have emphasized the utilization of phosphate tethers to mediate reactions in a chemo- and diastereoselective fashion, with recent work incorporating one-pot, sequential protocols to the synthesis of 1,3- anti -diol containing natural products and complex polyols . To continue our efforts toward the development of modular and pot-economical approaches for the synthesis of complex molecules, we planned an asymmetric synthesis of Sch-725674 by carrying out a series of one-pot, sequential protocols in an overall minimal number of pots.…”