Kinetically controlled cyclocondensation of stereoisomeric and ring-chain tautomeric mixture of (±)-hydroxylactone and 0.5 equiv of ()-phenylglycinol provided tricyclic oxazoloisoindolone lactam (3,5a,9a,9b)-, a versatile intermediate for further stereocontrolled transformations to access enantiopure -fused octahydroisoindolones. An extension of this methodology was successfully applied to the synthesis of the 5,6-dihydroxy derivative (3a,5,6,7a)-.
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