Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I

Abstract

The stereoselective total synthesis of strongylodiol H and I has been accomplished. The synthetic procedure comprised the stereoselective reduction of a ketone functionality in an ene–yne–one employing CBS as a catalyst and a Cadiot–Chodkiewicz coupling reaction as the key reaction steps. A common aldehyde intermediate has been used for the synthesis of both strongylodiols.

Pitfalls in the structural elucidation of small molecules. A critical analysis of a decade of structural misassignments of marine natural products

“…The originally assigned conguration (6R) was disproved by stereoselective synthesis. 134 The conguration of strongylodiols H and I was originally reported as 6R, but the synthetic compounds showed the opposite optical rotation compared to the natural products, suggesting that the conguration was actually 6S (Fig. 21).…”

New 1,3-Diynoic Derivatives of Natural Lembehyne B: Stereoselective Synthesis, Anticancer, and Neuritogenic Activity

“…As a continuation of the studies dealing with stereoselective synthetic routes to lembehyne derivatives and the influence of their structure on the antitumor and neuritogenic activities, here, we report a stereoselective method for the synthesis of lembehyne B 1,3-diyne derivatives, close structural analogues of natural strongylodiols, − pellynols, and halicynones, which exhibit a broad range of biological activities. In addition, we planned to pay particular attention to testing of the antitumor and neuritogenic activities of the compounds by means of modern flow cytometry and phase-contrast microscopy.…”