THE SYNTHESIS OF 13-SPIRO-SUBSTITUTED PROTOBERBERINES VIA THE TANDEM ADDITION - CYCLIZATION REACTION OF 3-METHOXYPHTHALIDE ANIONS TO 3,4-DIHYDROISOQUINOLINES

Authors
WARRENER RN LIU LG RUSSELL RA TIEKINK ERT
Citation
Rn. Warrener et al., THE SYNTHESIS OF 13-SPIRO-SUBSTITUTED PROTOBERBERINES VIA THE TANDEM ADDITION - CYCLIZATION REACTION OF 3-METHOXYPHTHALIDE ANIONS TO 3,4-DIHYDROISOQUINOLINES, Synlett, (4), 1998, pp. 387
Citations number
4
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
4
Year of publication
1998
Database
ISI
SICI code
0936-5214(1998):4<387:TSO1PV>2.0.ZU;2-6
Abstract
The reaction of the anion of 3-methoxyphthalide with 3,4-dihydroisoqui nolines affords 13-spiro-substituted protoberberines rather than the e xpected 8,13-dioxo derivatives. Whilst the parent 3,4-dihydroisoquinol ine reacts stereospecifically to yield the (13S,13aS*) diastereomer, the 1-methyl derivative affords exclusively the (13R,13aS*) isomer. T his change in stereochemical outcome is attributed to conformational c hanges induced by the methyl group in the putative 8,13-dioxo-intermed iates.