Total Synthesis of Transtaganolide E and F: Insight in the Biosynthesis of the Transtaganolides. Issue 30 (11th September 2013)

• Record Type: Journal Article
• Authors: Larsson, Rikard; Scheeren, Hans W.; Aben, Rene W. M.; Johansson, Martin; Sterner, Olov
• Is Part Of: European journal of organic chemistry. Issue 30(2013)
• Page Start: 6955
• Page End: 6960
• Publication Date: 2013-09-11
• Subjects: Transtaganolides -- Rearrangement -- Cycloaddition -- Biosynthesis -- Natural products; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301092
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A total synthesis of transtaganolide E and F, proposed intermediates in the biosynthesis of the potent transtaganolides, including an Ireland–Claisen rearrangement and a high‐pressure intramolecular Diels–Alder cycloaddition reaction of an unactivated 2‐pyrone derivative, is reported. The implication of the results to the proposed transtaganolides biosynthesis is discussed. Abstract : The total synthesis of transtaganolide E and F through an Ireland–Claisen rearrangement and a high‐pressure Diels–Alder cycloaddition reaction sequence from a proposed achiral biosynthetic intermediate is reported. The implication of our results to the suggested biosynthesis of the transtaganolides is discussed.