Stereocontrolled Synthesis of an Indole Moiety of Sespendole and Stereochemical Assignment of the Side Chain

Two possible diastereomers of the indole moiety of sespendole were synthesized from 3-hydroxy-4-nitrobenzaldehyde in a highly stereoselective manner. Comparison of ¹H and ¹³C NMR spectra of the two synthetic materials with those sespendole leads us to propose that the relative stereochemistry of the epoxyalcohol is <i>syn</i>

Stereocontrolled Synthesis of an Indole Moiety of Sespendole and Stereochemical Assignment of the Side Chain

Two possible diastereomers of the indole moiety of sespendole were synthesized from 3-hydroxy-4-nitrobenzaldehyde in a highly stereoselective manner. Comparison of ¹H and ¹³C NMR spectra of the two synthetic materials with those sespendole leads us to propose that the relative stereochemistry of the epoxyalcohol is <i>syn</i>

Base-Mediated Cascade Cyclization: Stereoselective Synthesis of Benzooxazocinone

A new strategy for the synthesis of the oxa-azabicyclo[3.3.1]­nonane subunit, a component of the naucleamide E core structure, has been developed. This annulation reaction between 1-substituted 3,4-dihydroisoquinolines and coumarin derivatives conveniently affords the oxa-azabicyclo[3.3.1]­nonane framework via a base-mediated cascade cyclization under aqueous conditions. The value of this work lies in the efficient formation of the oxa-azabicyclo[3.3.1]­nonane skeleton via a process whereby all the C–C, C–O, and C–N bond formations occur in a single chemical operation. In addition, the subsequent ring opening of these compounds furnished pyridoisoquinoline derivatives