[Angew. Chem. Int. Ed.] Prof. Yandong Zhang published a paper entitled “Total Synthesis of Aplydactone by a Conformationally Controlled C−H Functionalization”-College of Chemistry and Chemical Engineering

[Angew. Chem. Int. Ed.] Prof. Yandong Zhang published a paper entitled “Total Synthesis of Aplydactone by a Conformationally Controlled C−H Functionalization”

Publish Date:07.June 2017 Visted: Times

Title: Total Synthesis of Aplydactone by a Conformationally Controlled C−H Functionalization

Author: Chenguang Liu, Renzhi Chen, Yang Shen, Zhanhao Liang, Yuhui Hua, Prof. Dr. Yandong Zhang*

Abstract:
A concise, protecting-group-free total synthesis of the unusual brominated sesquiterpene aplydactone is described. Our synthesis features a [2+2] photocycloaddition, a Wolff ring contraction, an unusual remote C−H functionalization to establish the highly strained tetracyclic core, and a hydrogen-atom transfer (HAT) reaction to access the bromine-containing stereocenter. A finely tuned conformation of the α-diazoketone precursor is the key for the success of the late-stage transannular C−H insertion to deliver a bridged six-membered ring and a quaternary stereocenter (C6) between two quaternary carbon atoms (C1 and C7).

Full Link: http://onlinelibrary.wiley.com/doi/10.1002/anie.201703803/full

Address：College of Chemistry and Chemical Engineering, Xiamen University, Fujian Province
Zipcode：361005 Tel:0592-2186405 E-mail：chem-xmu@xmu.edu.cn
Copyright © College of Chemistry and Chemical Engineering 2023 All Rights Reserved

Research Highlights

[Angew. Chem. Int. Ed.] Prof. Yandong Zhang published a paper entitled “Total Synthesis of Aplydactone by a Conformationally Controlled C−H Functionalization”