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Abstract
A dehydrative annulation strategy involving an intramolecular ring closure under a Mitsunobu-type reaction condition has been used for the construction of octahydroindolizine framework successfully. This strategy that was reported to be unsuccessful when applied to a similar system allowed us to perform a diastereoselective synthesis of (6R,8aS)-octahydroindolizin-6-ol [a precursor of (–)-8a-epidesacetoxyslaframine] starting from commercially available chiral (S)-epichlorohydrin via a piperidine intermediate, i.e., (3R,6S)-6-(3-hydroxypropyl)piperidin-3-ol. The methodology has potential to afford a library of optically pure small molecules of pharmacological importance based on the related indolizine framework.
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