A Paternò−Büchi Approach to the Synthesis of Merrilactone A
- 11 August 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (18), 3969-3971
- https://doi.org/10.1021/ol0514496
Abstract
A six-step approach to the tetracyclic core of merrilactone A is described that uses an intramolecular Paterno-Büchi photoaddition to install the key oxetane ring. Irradiation of bicyclic enone 16, constructed through cyclopentenone alkylation followed by a domino oxy-/carbopalladation reaction, produces the tetracyclic oxetane 17 in excellent yield, having the core carbon skeleton of the target compound merrilactone A. [reaction: see text]Keywords
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