Facile Synthesis of the Tricyclic Core of Sarain A. 3-Oxidopyridinium Betaine Cycloaddition Approach1
Organic Letters1999Vol. 1(12), pp. 2017–2019
Citations Over TimeTop 22% of 1999 papers
Abstract
[formula: see text] A new approach to a suitably functionalized tricyclic core of sarains has been developed by means of Katritzky's cycloaddition using 3-oxidopyridinium betaines. A key step was the regioselective differentiation of the two nearly identical hydroxy groups derived from oxidative cleavage of the double bond in 8 to afford 14. A stereocontrolled construction of the tricyclic core 20 of sarains containing the requisite side chain at C-3' was achieved by an intramolecular conjugate addition.
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