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Synthesis of the phthalide isoquinoline alkaloids levo egenine levo corytensine and levo bicuculline by asymmetric carbonyl addition of chiral dipole stabilized organometallics

Synthesis of the phthalide isoquinoline alkaloids levo egenine levo corytensine and levo bicuculline by asymmetric carbonyl addition of chiral dipole stabilized organometallics

Journal of Organic Chemistry 56(4): 1564-1569

The asymmetric addition of metalated [(methylenedioxy)isoquinolyl]oxazolines is 100% selective for the erythro (.alpha.-hydroxybenzyl)isoquinoline diastereomers, with 2:1 selectivity of the two possible erythro stereoisomers. Enrichment to 100% ee after removal of the auxiliary and conversion to (-)-bicuculline and (+)-bicuculline diol establish the absolute configuration of the major addition product. Inversion of the C-9 hydroxyl affords entry into the threo series as well. The asymmetric carbonyl addition was used to synthesize, for the first time, the phthalide-isoquinoline hemiacetals corytensine and egenine, confirming the previously assigned structures and absolute configurations, and establishing the identity of egenine with decumbensine and of corytensine with epi-.alpha.-decumbensine.

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Accession: 007860258

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