Tunable Cyclization Strategy for the Synthesis of Zizaene-, allo-Cedrane-, seco-Kaurane-, and seco-Atesane-Type Skeletons

Org Lett. 2017 Oct 6;19(19):5324-5327. doi: 10.1021/acs.orglett.7b02610. Epub 2017 Sep 21.

Abstract

A versatile Lewis acid-mediated cyclization strategy has been developed for selectively establishing zizaene-, allo-cedrane-, seco-kaurane-, and seco-atesane-type skeletons. The zizaene- and seco-atesane-type skeletons can be obtained in a cascade manner, which involves Diels-Alder reaction of cyclic enones with bis-silyloxy dienes and carbocyclization of yne-enolates through Lewis acid dependent 5- or 6-exo-dig modes. This cyclization strategy was also employed for the core synthesis of tashironin.

Publication types

  • Research Support, Non-U.S. Gov't