Synthetic Communications p. 500 - 506 (2014)
Update date:2022-09-26
Topics:
Samala, Ramakrishna
Gurram, Venkateshwarlu
Patro, Balaram
Pottabathini, Narender
Mukkanti
A convenient and facile enantioselective synthesis of (-)-erinapyrone B from commercially available D-(+)-malic acid has been achieved in seven steps. One of the key steps in this synthesis was the one-pot reaction of palladium(II)-mediated Wacker-type oxidative cyclization in the presence of a catalytic amount of p-toluenesulphonic acid (p-TsOH) which has been found to be effective for the preparation of enantiopure 2,3-dihydro-4H-pyran-4-one from the corresponding enantiopure β-hydroxyenone via enantio-enriched diketohydroxy intermediate.
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