期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 9, 期 1, 页码 260-270出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200390019
关键词
asymmetric synthesis; lactones; metathesis; natural products; total synthesis
The development of a new method for the enantioselective synthesis of disubstituted gamma-butyrolactones is reported. Based on this strategy, the total synthesis of three paraconic acids, that is (-)-roccellaric acid, (-)-nephrosteranic acid and (-)protopraesorediosic acid, and the formal total synthesis of (-)-methylenolactocin and (-)-protolichesterinic acid is described, which are important because of their antibiotic and antitumor properties. Key steps of the synthesis are copper(I) -catalyzed asymmetric cyclopropanations of furans, highly diastereoselective Sakurai allylations, Lewis acid or Lewis base catalyzed retroaldol/lactonization cascades, and ruthenium(II)-catalyzed, intermolecular cross metathesis reactions.
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