ChemInform Abstract: Novel Synthesis of Nectrisine and 4-epi-Nectrisine.

✍ Scribed by Y. J. KIM; T. KITAHARA

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 29 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199733322

✦ Synopsis

Novel Synthesis of Nectrisine and 4-epi-Nectrisine.

-Nectrisine (VIII), a potent inhibitor of glycosidase, is prepared by a new route starting from D-(-)-diethyl tartrate. Key step is the reduction of a lactam precursor to the amino alcohol. Since all attempts to reduce lactam (IV) are unsuccessful, the Pmb group is replaced by Boc. The product (VI) thus obtained reacts cleanly to the desired (VII). An analogous procedure is applied in the synthesis of the 4-epi analogue of (VIII). -(KIM, Y.