Work

An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol

Year: 2018

Type: article

Abstract: An approach to synthesize the pentacyclic framework of the polyol diterpenoid ryanodol is reported. The ABC tricycle was constructed by a Co-mediated Pauson–Khand reaction, and both radical and anionic cyclization pathways were developed to form the E-ring. In addition, a reaction sequence involving SeO 2 -mediated enone oxidation and hydroxyl-directed oxy-Michael addition was developed to introduce the A-ring oxidation. The feasibility of forming the bridging D-ring by an oxidative dearomatization was established.

Source: Organic Letters

DOI: 10.1021/acs.orglett.8b01387

Authors: Chen Xu, Arthur Han, Sarah E. Reisman

Institutions: California Institute of Technology, Southern University of Science and Technology

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Eli Lilly and Company, Novartis, National Institute of General Medical Sciences