Cationic Polyene Cyclization for Taiwaniaquinoid Construction. Issue 4 (1st February 2017)

• Record Type: Journal Article
• Authors: Graham, Marlowe; Baker, Robert W.; McErlean, Christopher S. P.
• Is Part Of: European journal of organic chemistry. Issue 4(2017)
• Page Start: 908
• Page End: 913
• Publication Date: 2017-02-01
• Subjects: Cyclization -- Fused‐ring systems -- Carbocycles -- Diastereoselectivity -- Natural products; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201601349
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : An acid‐catalyzed polyene cyclization has been used to rapidly generate the 6/5/6‐fused ring system of the taiwaniaquinoid natural products. The cis ‐fused diastereomer was formed selectively, which enabled a step‐efficient synthesis of (±)‐5‐ epi ‐taiwaniaquinone G. Abstract : The cationic polyene cyclization of a geranylbenzene derivative gave a surprising stereochemical outcome, which was subsequently rationalized by using computational methods. This cyclization enabled a step‐efficient synthesis of 5‐ epi ‐(±)‐taiwaniaquinone G.