doi: 10.1021/ol0514496.
A Paterno-Büchi approach to the synthesis of merrilactone A
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- PMID: 16119944
- DOI: 10.1021/ol0514496
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A Paterno-Büchi approach to the synthesis of merrilactone A
Org Lett.
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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]
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