Synfacts 2010(1): 0014-0014  
DOI: 10.1055/s-0029-1218395
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Pallavicinolide

Contributor(s): Philip Kocienski, Indu Dager
J.-Q. Dong, H. N. C. Wong*
The Chinese University of Hong Kong, P. R. of China
Further Information

Publication History

Publication Date:
21 December 2009 (online)

Significance

Pallavicinolide A is isolated from the liverwort Pallavicinia subciliata. Notable features of this biomimetic synthesis are (1) a singlet oxygen oxidation of furan G to form butenolide H and (2) an intramolecular Diels-Alder cycloaddition using Nicolaou’s IBX protocol to afford fused bicycle J.