Sesterterpenoids

Total Synthesis of Terpenes and Their Biological Significance: A Critical Review

“…To make decalin (176), we started via Robinson annulation between (+)-( 175) (dihydro carvone) and (174) (ethyl vinyl ketone). After the annulation event, exposing the mixture to an O2 atmosphere leads to installation of the alcohol at the C-6 (Ƴ-position) diastereoselectively.…”

“…After the annulation event, exposing the mixture to an O2 atmosphere leads to installation of the alcohol at the C-6 (Ƴ-position) diastereoselectively. In one step, in a sequence involving bromination and elimination, dienone (177) from decalin (176) was efficiently obtained in an 85% yield. Diol (178) was obtained in a 60% yield by hydrolysis of (177) with Burgess solution and dihydroxylation via chemoselective/diastereoselective 5:1 ratio with AD-mix-α of terminal olefin.…”

“…On a number of cell lines, it also displayed remarkable but inert cytotoxic effects with an IC 50 range of 0.057-3.4 µM in vitro. It also influences the transcriptional level of multiple pathways associated with cell survival, such as in apoptosis, cell cycle, and inflammation [176].…”