Synfacts 2007(7): 0669-0669  
DOI: 10.1055/s-2007-968603
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Merrilactone A

Contributor(s):Philip Kocienski, Stewart Eccles
W. He, J. Huang, X. Sun, A. J. Frontier*
University of Rochester, USA
Total Synthesis of (±)-Merrilactone A via Catalytic Nazarov Cyclization
J. Am. Chem. Soc.  2007,  129:  498-499  
Further Information

Publication History

Publication Date:
22 June 2007 (online)


Significance

Merrilactone A is a sesquiterpene dilactone isolated from Illicium merrillianum. The complex tricyclic system containing three quaternary centers was synthesized using a Nazarov and radical cyclization.

Review

For a review of Nazarov cyclizations, see: Some New Nazarov Chemistry M. A. Tius Eur. J. Org. Chem. 2005, 2193-2206.

Comment

Silyloxyfuran D underwent a catalytic Nazarov cyclization, where the cationic intermediate was quenched by the silylenol ether resulting in unsaturated bicyclic lactone F and two quaternary centers. A selective deprotection of the TMS group followed by radical cyclization of F gave G and the third quarternary center in the highly complex core of merrilactone.