Total Synthesis of (+)-Cyclobutastellettolide B
Zhongchao Zhang, Sijia Chen, Fu Tang, Kai Guo, Xin‐Ting Liang, Jun Huang, Zhen Yang
Abstract
A convenient enantioselective total synthesis of (+)-cyclobutastellettolide B via a strategy that involves a diastereoselective Johnson-Claisen rearrangement, a regioselective cyclopropoxytrimethylsilane ring-opening reaction, and a Norrish-Yang cyclization is described. The results of computational and experimental studies indicate that the regio- and stereoselectivity of the Norrish-Yang reaction are controlled by the C-H bond dissociation energy and restricted rotation of the C13-C14 bond.
Topics & Concepts
ChemistryRegioselectivityEnantioselective synthesisStereoselectivityStereochemistryBond cleavageClaisen rearrangementTotal synthesisDissociation (chemistry)Organic chemistryCatalysisCatalytic C–H Functionalization MethodsAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and Catalysis