Search

Nonactivated trienes and aryltrienes were cyclized into polycyclic compounds in good to excellent yields under bismuth triflate catalysis in a biomimetic fashion. The reaction showed broad applicability and allowed for the formation of functionalized bicyclic to tetracyclic structures from simple precursors in one pot. For some specific substrates, the cyclization was followed by a methyl shift as encountered in terpenoid biosynthesis. [ABSTRACT FROM AUTHOR]

A biosynthetically inspired synthesis of ()-liphagal has been achieved from ()-sclareolide in 13 steps (9% overall yield). The key step is a biomimetic ring expansion of a highly stabilized benzylic carbocation, which generates the seven-membered ring and the benzofuran of the natural product in a single cascade reaction. [ABSTRACT FROM AUTHOR]

A unified strategy for the chemical synthesis of the icetexane diterpenoids brussonol and 5,6-dihydro-6-hydroxysalviasperanol has led to a structural revision of the recently isolated natural products abrotandiol and abrotanone. [ABSTRACT FROM AUTHOR]

The article presents a study which examines the effect of 1-deoxy-xylulose-5-phosphate (DXP) reductoisomerase-catalyzed reaction through a secondary kinetic isotope. It explores the evidence for a retroaldol-aldol rearrangement. Under the study, terpenoids are biosynthesized with two 5-carbon isoprene units, isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP).