Abstract
An asymmetric total synthesis of eicosanoid 4 starting from 2,2-dimethyl-(R)-1,3-dioxolane-4- carbaldehyde is described. The key steps involved for the synthesis include modified Simmons- Smith cyclopropanation, stereoselective reduction, ring-closing metathesis (RCM) and Nozaki- Hiyama-Kishi coupling reaction.
Highlights
As a part of defense mechanism, marine organisms produce a fascinating range of secondary metabolites endowed with unusual and unexpected biological profiles
The arachidonic acid pathway in marine organisms provided a number of oxylipins such as 1-3 containing the cyclopropyl-lactone groups
In conjunction with other marine fatty acid metabolites (Figure 1),3 eicosanoid 4 incorporate a cyclopropanelactone motif and lipoxygenase inhibiting activity and provoked a considerable synthetic interest.4a,g It is likely that the origin of eicosanoid 4 might have occurred from transformation analogous to that as constanolactones 3.2 To expedite current pharmaceutical evaluations of this family, we describe an asymmetric total synthesis of eicosanoid 4
Summary
As a part of defense mechanism, marine organisms produce a fascinating range of secondary metabolites endowed with unusual and unexpected biological profiles. Combined organic extracts were dried over Na2SO4 and purified by silica gel column chromatography using ethyl acetate/petroleum ether (1:4) to obtain 5.43g (86%) of pure allyl alcohol 10 as colorless viscous liquid. Combined organic extracts were washed successively with water and brine, dried over Na2SO4 and purified by silica gel column chromatography using 5% ethyl acetate/petroleum ether to afford 10.0g (80%) of pure silyl ether 11 as colorless liquid.
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