Journal
ORGANIC LETTERS
Volume 15, Issue 11, Pages 2696-2699Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol400999a
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Funding
- Spanish MINECO [CTQ2011-23620]
- Generalitat de Catalunya [2009SGR 00901]
- IRB Barcelona
- MICINN
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A new approach to the synthesis of 4,5-disubstituted cyclopentenones is described. The strategy is based on the Pauson-Khand (PK) reaction of norbornadiene and N-Boc-propargylamine as an alkyne with a masked leaving group, which can be eliminated at will. This approach to the synthesis of 4,5-disubstituted cyclopentenones overcomes the problem of using the alkylation to introduce the alpha side chain. As an example, prostane 13-epi-12-oxo-phytodienoic acid (13-epi-12-oxo-PDA) methyl ester was synthesized.
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