Bridged-Type Selective Intramolecular Nitrone–Alkene Cycloaddition: Computational Chemistry-Inspired Regioselectivity Control

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 4, 2025

A regioselective intramolecular nitrone-alkene cycloaddition for synthesizing oxazabicyclo ring-fused indoles is reported. Computational studies guided the development of optimal conditions using In(OTf)3 as a Lewis acidic reagent. This method demonstrates broad substrate scope, forming seven- and eight-membered carbocycles with various substituents, provides versatile route to complex nitrogen-containing scaffolds potential applications in medicinal chemistry total synthesis biologically active compounds.

Language: Английский

A Short Synthesis of (−)‐6,7‐Secoagroclavine via Metal‐Free Reductive Coupling

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(13)

Published: Feb. 16, 2024

Abstract A concise, convergent, and enantioselective synthesis of (−)‐6,7‐secoagroclavine, a pivotal intermediate in the both clavine ergot alkaloids, was accomplished from derivative renowned Uhle's ketone. The is centered on metal‐free reductive coupling tosylhydrazone protected 4‐amino ketone commercially available 2,2‐dimethylethenylboronic acid, which used as four‐carbon building block. This novel approach directly sets stereochemistry difficult‐to‐access aryl vinyl methane carbon stereogenic center (−)‐6,7‐secoagroclavine.

Language: Английский