A Concise Total Synthesis of (+)‐Waihoensene Guided by Quaternary Center Analysis
Cheng Peng, Piyush Arya, Zhiyao Zhou, Scott A. Snyder
Abstract
Abstract The four contiguous all‐carbon quaternary centers of waihoensene, coupled with the absence of any traditional reactive functional groups other than a single alkene, render it a particularly challenging synthetic target among angular triquinane natural products. Here, we show that its polycyclic frame can be assembled concisely by using a strategically chosen quaternary center to guide the formation of the other three through judiciously selected C−C bond formation reactions. Those events, which included a unique Conia‐ene cyclization and a challenging Pauson–Khand reaction, afforded a 17‐step synthesis of the molecule in enantioenriched form.
Topics & Concepts
Quaternary carbonAlkeneQuaternaryTotal synthesisChemistryFunctional groupCenter (category theory)Combinatorial chemistryStereochemistryOrganic chemistryEnantioselective synthesisCatalysisBiologyCrystallographyPaleontologyPolymerChemical synthesis and alkaloidsMarine Sponges and Natural ProductsSynthetic Organic Chemistry Methods