An Approach to the Bicyclic C‐5–C‐17/C‐19–C‐20 (BC) Portion of Neoclerodane Diterpenes by Intramolecular Diels–Alder Reaction1. Issue 19 (8th May 2014)

• Record Type: Journal Article
• Authors: Wang, Yuzhou; Rogachev, Victor; Wolter, Martin; Gruner, Margit; Jäger, Anne; Metz, Peter
• Is Part Of: European journal of organic chemistry. Issue 19(2014)
• Page Start: 4083
• Page End: 4088
• Publication Date: 2014-05-08
• Subjects: Cycloaddition -- Michael addition -- Cross‐coupling -- Natural products -- Terpenoids; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402165
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Using a highly diastereoselective intramolecular acrylate [4+2] cycloaddition as the key step, a short route from 3‐furaldehyde to a bicyclic building block for the synthesis of neoclerodane diterpenes was developed. A first attempt featuring a conjugate methylation of a dienyl lactone failed, but a streamlined sequence using an all‐encompassing intramolecular Diels–Alder reaction of a sterically congested 1, 3‐diene was successful. Abstract : A highly diastereoselective intramolecular acrylate [4+2] cycloaddition of a sterically congested 1, 3‐diene served as the key step in a short synthesis of a BC building block for neoclerodane diterpenes.