Work

A Strategy for the Convergent and Stereoselective Assembly of Polycyclic Molecules

Year: 2018

Type: article

Abstract: The stereoselective oxidative coupling of cyclic ketones via silyl bis-enol ethers followed by ring-closing metathesis is shown to be a general and powerful reaction sequence for the preparation of diverse polycyclic scaffolds from simple precursors. The modular strategy successfully constructs substructures prevalent in numerous bioactive natural product families, varying in substitution and carbocyclic composition. Several of the prepared compounds were shown to possess potent cytotoxic activity against a panel of tumor cell lines. The utility of this strategy was further demonstrated by a concise and highly convergent 17-step formal synthesis of the complex antimalarial marine diterpene, (+)-7,20-diisocyanoadociane.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.7b13234

Authors: Emily E. Robinson, Regan J. Thomson

Institution: Northwestern University

Language: English

Topic: Synthetic Organic Chemistry Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: American Cancer Society, Northwestern University

Award: G5811398668