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Total synthesis of marine natural products separacenes A and B.
Organic & Biomolecular Chemistry 2017 June 8
A short and convergent route for the stereoselective total synthesis of separacenes A and B has been developed using (+)-methyl d-lactate and d-(-)-tartaric acid as the chiral pools. The characteristic features of this synthesis include the Trost-Rychnovsky alkyne rearrangement to construct the C7 -C9 conjugated diene, the Horner-Wadsworth-Emmons olefination to form the C5 -C6 and C11 -C12 olefins and the Corey-Bakshi-Shibata reaction to install the C-13 hydroxy functionality.
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