Bowen Fang

Au-Catalyzed Piperidine Synthesis via Tandem Acyloxy Migration/Intramolecular [3+2] Cycloaddition of Enynyl Esters

An Au-catalyzed tandem protocol involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach for the synthesis of polyfunctional piperidines, which are subunits of many bioactive molecules.

Tandem Oxidative Dearomatization/Intramolecular Diels–Alder Reaction for Construction of the Tricyclic Core of Palhinine A

A concise construction of the 6/6/5 tricyclic core of Lycopodium alkaloid palhinine A (1) has been accomplished. The developed synthetic strategy featured a tandem oxidative dearomatization/intramolecular Diels-Alder reaction to construct C/D rings and an intramolecular 5-exo-trig radical cyclization to install the B ring of palhinine A (1). The developed approach paves the way for the total synthesis of palhinine A (1).

Asymmetric Total Synthesis of Fusarentin 6-Methyl Ether and Its Biomimetic Transformation into Fusarentin 6,7-Dimethyl Ether, 7-O-Demethylmonocerin, and (+)-Monocerin

A concise asymmetric total synthesis of a fusarentin ether (1) with sequential biomimetic transformation to its analogues fusarentin 6,7-dimethyl ether (2), 7-O-demethylmonocerin (3), and (+)-monocerin (4) has been accomplished. The cis-fused furobenzopyranones of 7-O-demethylmonocerin (3) and (+)-monocerin (4) were efficiently constructed via an intramolecular nucleophilic trapping of a quinonemethide intermediate, which was obtained by benzylic oxidation of fusarentin 6-methyl ether (1) using hypervalent iodine reagent.

Rapid Construction of the [6-6-6-5] Tetracyclic Skeleton of the Daphniphyllum Alkaloid Daphenylline

You can call me Al: A concise route for construction of the [6-6-6-5] tetracyclic skeleton of daphenylline, a structurally novel Daphniphyllum alkaloid, has been developed with full stereocontrol in only 8 steps from two known fragments. This approach features an intramolecular [3+2] cycloaddition of a 2-azaallyl anion with an alkene to form the cis-fused AC rings.

Asymmetric Total Synthesis of Cladosporin and Isocladosporin

The first asymmetric total syntheses of cladosporin and isocladosporin were accomplished in 8 steps with 8% overall yield and 10 steps with 26% overall yield, respectively. The relative configuration of isocladosporin was determined via this total synthesis.

CCDC 881449: Experimental Crystal Structure Determination

Related Article: Huaiji Zheng, Changgui Zhao, Bowen Fang, Peng Jing, Juan Yang, Xingang Xie, and Xuegong She|2012|J.Org.Chem.|77|5656|doi:10.1021/jo300805n