Enantioselective Total Synthesis of Desbromoarborescidines A–C and the Formal Synthesis of (<i>S</i>)‑Deplancheine

Starting from Boc-protected tryptamine and (<i>S</i>)-tetrahydro-5-oxo-2-furancarboxylic acid, facile enantioselective total synthesis of desbromoarborescidines A–C and the formal synthesis of (<i>S</i>)-deplancheine have been accomplished via a common intermediate (<i>S</i>)-indolo­[2,3-<i>a</i>]­quinolizine. Synthesis of enantiomerically pure (<i>S</i>)-acetoxyglutarimide, stereoselective reductive intramolecular cyclization, hydroxyl group-assisted in situ <i>N</i>-Boc-deprotection, selective deoxygenation of the xanthate ester, and lactam hydrolysis followed by an appropriate exchange of nitrogen regioselectivity in intramolecular cyclization were the decisive steps

Enantioselective Total Synthesis of Desbromoarborescidines A–C and the Formal Synthesis of (<i>S</i>)‑Deplancheine

Starting from Boc-protected tryptamine and (<i>S</i>)-tetrahydro-5-oxo-2-furancarboxylic acid, facile enantioselective total synthesis of desbromoarborescidines A–C and the formal synthesis of (<i>S</i>)-deplancheine have been accomplished via a common intermediate (<i>S</i>)-indolo­[2,3-<i>a</i>]­quinolizine. Synthesis of enantiomerically pure (<i>S</i>)-acetoxyglutarimide, stereoselective reductive intramolecular cyclization, hydroxyl group-assisted in situ <i>N</i>-Boc-deprotection, selective deoxygenation of the xanthate ester, and lactam hydrolysis followed by an appropriate exchange of nitrogen regioselectivity in intramolecular cyclization were the decisive steps

Copper(I)-catalyzed cascade synthesis of 2-substituted 1,3-benzothiazoles: direct access to benzothiazolones

An efficient cascade process for the preparation of 2‐substituted 1,3‐benzothiazoles directly from 2‐haloaryl isothiocyanates and O or S nucleophiles by a Cu‐catalyzed, intramolecular, C–S bond formation has been developed. This cascade method is viable for the efficient syntheses of both O‐ and S‐substituted 1,3‐benzothiazoles. Furthermore, 1,3‐benzothiazol‐2(3H)‐ones having an alkyl group allow easy access to 1,3‐benzothiazolones