A Bioinspired Cyclization Sequence Enables the Asymmetric Total Synthesis of Dictyoxetane

Hugelshofer, Cedric L. and Magauer, Thomas (2016): A Bioinspired Cyclization Sequence Enables the Asymmetric Total Synthesis of Dictyoxetane. In: Journal of the American Chemical Society, Vol. 138, No. 20: pp. 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.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy
• Subjects: 500 Science > 540 Chemistry
• ISSN: 0002-7863
• Language: English