Total Synthesis of (+)‐Neomarinone |
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Authors: | Miguel Peña‐López M Montserrat Martínez Dr Luis A Sarandeses Prof Dr José Pérez Sestelo Prof Dr |
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Institution: | 1. Departamento de Química Fundamental, Universidade da Coru?a, Campus Zapateira, s/n;2. 15071A Coru?a (Spain), Fax: (+34)?34‐981‐167‐065 |
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Abstract: | The first total synthesis of (+)‐neomarinone has been achieved by following a concise and convergent route using methyl (R)‐lactate and (R)‐3‐methylcyclohexanone as chiral building blocks. Key steps of the synthesis are the stereocontrolled formation of the two quaternary stereocenters by diastereoselective 1,4‐conjugate addition and enolate alkylation reactions, and the construction of the furanonaphthoquinone skeleton by regioselective Diels–Alder reaction between a 1,3‐bis(trimethylsilyloxy)‐1,3‐diene and a bromoquinone. The synthesis proves the relative and absolute stereochemistry of natural neomarinone. |
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Keywords: | alkylations asymmetric synthesis cuprate additions Diels– Alder reaction natural products |
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