Total Synthesis and Structure Revision of Saniculamoid D

We present the first asymmetric total synthesis of the norsesquiterpenoid saniculamoid D, from a previously known pure chiral imide, with a longest linear sequence of seven steps. The key highlight of the synthesis is the formation of the bicyclo[3.1.0]hexane moiety through the Julia–Kocienski olefination and Hodgson cyclopropanation. Notably, the NMR spectra and specific rotation value of the synthesized structure did not agree with those of the natural compound. However, a meticulous comparison of the data prompted the reassignment of the correct structure of saniculamoid D, which now corresponds to the structure initially proposed for chromolaevanedione. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - September 15, 2023 Category: Chemistry Authors: Ota, Koichiro Kamaike, Kazuo Miyaoka, Hiroaki Tags: letter Source Type: research