Department of Chemistry and Biochemistry, Florida Atlantic University , Boca Raton, Florida 33431, United States.
Org Lett. 2017 Feb 3;19(3):576-579. doi: 10.1021/acs.orglett.6b03689. Epub 2017 Jan 12.
A biomimetic synthesis of briareolate ester B (3) from briareolate ester L (1) via the intermediate briareolate ester G (2) has been achieved through a unique transannular oxa-6π electrocyclization induced by UVA light. UVC irradiation of 3 triggered a rapid retro-6π electrocyclization to establish an unprecedented photochromic switch. In the ground state, reaction of 1 led to the formation of a polycyclic γ-spiroketal γ-lactone 5, architecturally related to the ether-bridged cembranoids of the cladiellin class.
通过独特的 UVA 光诱导的反环[6,6]氧杂-π 电环化反应，从 briareolate 酯 L（1）出发仿生合成了 briareolate 酯 B（3）。3 经 UVC 照射后迅速发生逆[6,6]电环化反应，建立了一个前所未有的光致变色开关。在基态下，1 反应生成了一个多环γ-螺环缩酮γ-内酯 5，其结构与 cladiellin 类的醚桥碳烯类似。
