Work

A Concise Synthesis of (−)‐Aplyviolene Facilitated by a Strategic Tertiary Radical Conjugate Addition

Year: 2012

Type: article

Abstract: A second-generation synthesis of the rearranged spongian diterpene aplyviolene is reported. The key step is the addition of a trialkyl tertiary radical generated by photoredox-mediated fragmentation of a N-(acyloxy)phthalimide to an α-chloropentenone (see scheme). This process fashioned a quaternary stereocenter while combining two units of significant complexity.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201204977

Authors: Martin J. Schnermann, Larry E. Overman

Institution: University of California, Irvine

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Cancer Institute, National Institute of General Medical Sciences, National Institute of Neurological Disorders and Stroke

Awards: New Methods for the Synthesis of Neurological Agents, New Methods for the Synthesis of Neurological Agents and Other Heterocyclic Molec, Enatioselective Synthesis of Gardneria Oxindole Natural Products