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. 2014 Oct 7:10:2332-2337.
doi: 10.3762/bjoc.10.242. eCollection 2014.

A modular phosphate tether-mediated divergent strategy to complex polyols

Paul R Hanson  1 , Susanthi Jayasinghe #  1 , Soma Maitra #  1 , Cornelius N Ndi  1 , Rambabu Chegondi  1
Affiliations

A modular phosphate tether-mediated divergent strategy to complex polyols

Paul R Hanson et al. Beilstein J Org Chem. .

Abstract

An 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.

Keywords: one-pot; organophosphorus; phosphate-tether; polyol; sequential processes; stereodivergent.

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Figures

Scheme 1
Scheme 1
The 3-component coupling strategy.
Figure 1
Figure 1
Synthesis of trienes 5–7.
Scheme 2
Scheme 2
Synthesis of polyols 10–14 in one-, two-pot sequential protocols.
Scheme 3
Scheme 3
Synthesis of polyols 17–21 in one-, two-pot sequential protocols.
See this image and copyright information in PMC

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