BICYCLO[3.3.1]NONANES AS SYNTHETIC INTERMEDIATES .21. ENANTIODIVERGENT SYNTHESIS OF THE CIS,CIS 2,6-DISUBSTITUTED PIPERIDIN-3-OL CHIRAL BUILDING-BLOCK FOR ALKALOID SYNTHESIS

Authors
MOMOSE T TOYOOKA N JIN M
Citation
T. Momose et al., BICYCLO[3.3.1]NONANES AS SYNTHETIC INTERMEDIATES .21. ENANTIODIVERGENT SYNTHESIS OF THE CIS,CIS 2,6-DISUBSTITUTED PIPERIDIN-3-OL CHIRAL BUILDING-BLOCK FOR ALKALOID SYNTHESIS, Journal of the Chemical Society. Perkin transactions. I, (13), 1997, pp. 2005-2013
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
13
Year of publication
1997
Pages
2005 - 2013
Database
ISI
SICI code
0300-922X(1997):13<2005:BASI.E>2.0.ZU;2-2
Abstract
Enantiodivergent synthesis of the enantio-pure cis,cis 3-protected 2,6 -disubstituted piperidin-3-ol 1 has been achieved via a biochemical me thod, and the absolute stereochemistry of (+)-1 has been established b y its conversion into the known piperidine (-)-17. The utility of 1 as a chiral building block for alkaloid synthesis is demonstrated by the total synthesis of (-)-cassine and (+)-spectaline.