Stereocontrolled Synthesis of Enantiopure cis-Fused Octahydroisoindolones via Chiral Oxazoloisoindolone Lactams.

Kinetically controlled cyclocondensation of stereoisomeric and ring-chain tautomeric mixture of (±)-hydroxylactone 1 and 0.5 equiv of (R)-phenylglycinol provided tricyclic oxazoloisoindolone lactam (3R,5aS,9aR,9bS)-2a, a versatile intermediate for further stereocontrolled transformations to access enantiopure cis-fused octahydroisoindolones. An extension of this methodology was successfully applied to the synthesis of the 5,6-dihydroxy derivative (3aR,5R,6S,7aS)-17.

Citation

Alberto Marbán-González, Gaspar Maravilla-Moreno, Josué Vazquez-Chavez, Marcos Hernández-Rodríguez, Rodrigo Said Razo-Hernández, Mario Ordóñez, José Luis Viveros-Ceballos. Stereocontrolled Synthesis of Enantiopure cis-Fused Octahydroisoindolones via Chiral Oxazoloisoindolone Lactams. The Journal of organic chemistry. 2021 Dec 03;86(23):16361-16368

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PMID: 34738814

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