Aromatics to bis-triquinane: a tandem oxidative dearomatization of bis-phenol, cycloaddition, photorearrangement and a rapid entry into carbocyclic framework of Xeromphalinone E

Target Specific Tactics in Olefin Metathesis: Synthetic Approach to cis-syn-cis-Triquinanes and -Propellanes

“…Among these triquinane motifs, we plan to design new strategies to linear triquinanes and propellanes by a combined usage of ring-opening metathesis (ROM) and ring-closing metathesis (RCM) strategy. Selected methods reported for synthesis of triquinanes are metal mediated C–C bond cleavage, Weiss–Cook condensation, cascade radical cyclization, cycloadditions, photothermal metathesis, and oxa-di-π-methane rearrangement, etc. In view of our long-term interest in olefin metathesis, we conceived a new synthetic approach to tricyclopentanoid system based on ring-rearrangement metathesis (RRM) as a key step.…”

“…To generate stereochemical diversity in the final products one can use exo as well as endo DA adducts. Since bis­(triquinanes) are biologically active and pharmaceutically important building blocks, this methodology has been extended toward the synthesis of bis­(triquinane) derivatives.…”

Design and Synthesis of Linearly Fused Triquinanes through Tandem‐Metathesis: Access to Basic Core of Cucumin, Capnellene, Chondrosterin, and Xeromphalinone

“…Hirustene [4] is the simplest member of the cis‐anti‐cis triquinane family and its analogous compound, Hirustic acid C is the first naturally occurring linear triquinane in Nature (1947), which exhibits antibiotic and antitumor activities [5] . In addition, extensively studied triquinane natural products are coriolin, [6] hypnophilin, [7] pleurotellol & pleurotellic acid, [8] cucumin, [9] capnellene, [2a,10] chondrosterin, [11] and xeromphalinone [12] families because of their biological properties such as antibiotic and antitumor activities, etc.…”

Butterflyene: an entry into an aesthetically pleasing carbocycle via a Diels–Alder reaction on a tetrasubstituted olefin

“…In the present communication, we demonstrate a synthetic protocol towards acquisition of an interesting molecular geometry resembling the shape of a butterfly in four simple steps from cyclopentanone without using complex and fancy reagents. Based on our continued research interest in designing architecturally pleasing molecules, [12][13][14] we con-templated that the shape of an open-winged butterfly (Fig. 2a) could be envisioned as that in Fig.…”