Scandium-Catalyzed Skeleton Conversion of Lathyrane to Lathyranone-Type Euphorbia Diterpenes

J Org Chem. 2022 Oct 7;87(19):13411-13415. doi: 10.1021/acs.joc.2c01831. Epub 2022 Sep 20.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Diterpenes*
  • Euphorbia*
  • Molecular Structure
  • Scandium
  • Skeleton

Substances

  • Diterpenes
  • lathyrane
  • Scandium