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DOI: 10.1055/s-2007-968603
Synthesis of (±)-Merrilactone A
Contributor(s):Philip Kocienski, Stewart EcclesUniversity of Rochester, USA
Total Synthesis of (±)-Merrilactone A via Catalytic Nazarov Cyclization
J. Am. Chem. Soc. 2007, 129: 498-499
Publication History
Publication Date:
22 June 2007 (online)
Key words
Nazarov cyclization - radical cyclization -
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.