Scandium-Catalyzed Skeleton Conversion of Lathyrane to Lathyranone-Type Euphorbia Diterpenes
Wei Cheng1, Jin-Bu Xu1, Neng Wang1
1Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu, Sichuan 610031, People's Republic of China.
Abstract:
Naturally occurring 1(15 → 14)abeo-lathyrane rearrangement-type diterpene lathyranone A (1) was prepared from lathyrane-type Euphorbia factor L11 (1a) via an efficient Sc(OTf)3/Et2NH-catalyzed α-ketol rearrangement, which was also suitable for the synthesis of lathyranones 2 and 3. This skeletal conversion strategy had the characteristic of biogenetically patterned synthesis and provided a convenient method for accessing naturally rare functionalized lathyranones from lathyranes. Moreover, the absolute configuration of the lathyranone skeleton was confirmed for the first time by the X-ray diffraction of 2.
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