rac-(2aS,2a¹ R,3aR,3a¹ S,5aS,6aR)-2a-Allyl-2,4-dichloro-2a,2a¹,3a¹,5a,6,6a-hexahydro-3aH-3-oxadicyclopenta[cd,gh]pentalen-3a-ol

Abstract

The title racemic triquinane, C14H14Cl2O2, is composed of four five-membered rings, one of which is a tetrahydrofuran ring to which an allyl group on one side and a hydroxyl group on the other side are attached. The core of the triquinane unit has a cis–syn–cis configuration. In the crystal, the molecules are linked by pairwise O—H...O hydrogen bonds, generating inversion dimers featuring R 2 2(8) loops.

Annulation Tactics of cis‐syn‐cis Triquinanes by Allylsilanes: Application of Hosomi‐Sakurai Reaction Conditions

“…When we attempted dechlorination using zinc in acetic acid under reflux conditions, we obtained a side product 31 , which was not reported earlier, along with the desired symmetrical triquinane 32 [29] . Previously, we treated triquinane 32 with allyl iodide/indium and trimethylsilyl chloride as an additive and observed 1,2‐adiition product [27d] . When the dichloro compound 32 was treated with trimethylallylsilane, we obtained a mixture as indicated by TLC.…”