期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 4, 页码 910-916出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200802021
关键词
alkylations; asymmetric synthesis; cuprate additions; Diels-Alder reaction; natural products
资金
- Xunta de Galicia [PG1DIT05BTF10301PR]
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 stereo-controlled formation of the two quaternary stereocenters by diastereoselective 1,4-conjugate addition and enolale alkylation reactions. and the construction of the furanonaphthoquinone skeleton by rcgioselective 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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