Total Synthesis of (+)-Cyclobutastellettolide B

• DOI: 10.1021/jacs.1c08880
• Publication Date: 2021-10-21T06:53:06Z
• Authors: Zhongchao Zhang; Sijia Chen; Fu Tang; Kai Guo; Xin-Ting Liang; Jun Huang; Zhen Yang
• Keywords: 01 natural sciences; 0104 chemical sciences

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.