A Bioinspired Cyclization Sequence Enables the Asymmetric Total Synthesis of Dictyoxetane

Hugelshofer, Cedric L. und Magauer, Thomas (2016): A Bioinspired Cyclization Sequence Enables the Asymmetric Total Synthesis of Dictyoxetane. In: Journal of the American Chemical Society, Bd. 138, Nr. 20: S. 6420-6423

Abstract

We have developed the first synthesis of the unique oxetane containing diterpene (+)-dictyoxetane. Our retrosynthetic planning was guided by the putative biosynthesis of the unprecedented 2,7-dioxatricyclo-[4.2.1.0(3,8])nonane ring system. A bioinspired 4-exo-tet, 5-exo-trig cyclization sequence enabled the construction of the synthetically challenging dioxatricyclic framework. The overall synthesis proceeds in 15 linear steps from a known and readily available trans-hydrindane fragment. In addition, we were able to realize the first dyotropic rearrangement of an epoxide-oxetane substrate.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0002-7863
• Sprache: Englisch