期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 14, 期 15, 页码 4675-4688出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200701991
关键词
balanol; metathesis; natural products; Protein kinase C inhibitors; total synthesis
Total syntheses of (-)-balanol and all of its stereoisomers starting from easily available Garner aldehydes are described. Diastereoselective Grignard reactions on Garner aldehydes and ring-closing metatheses are the key steps for the construction of hexahydroazepine subunits. The benzophenone subunits were constructed through coupling of suitably functionalized aromatic aldehyde and bromo components. The synthetic route constitutes a convenient and scalable reaction sequence to generate all of the stereoisomers of balanol. The methodology is explored further for the synthesis of N-tosyl analogues of balanol and of fully protected ophiocordin.
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