Bicyclo[3.3.1]nonanes as synthetic intermediates. Part 21.1 Enantiodivergent synthesis of the cis,cis 2,6-disubstituted piperidin-3-ol chiral building block for alkaloid synthesis
- 1 January 1997
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 13,p. 2005-2014
- https://doi.org/10.1039/a608490g
Abstract
Enantiodivergent synthesis of the enantio-pure cis,cis 3-protected 2,6-disubstituted piperidin-3-ol 1 has been achieved via a biochemical method, and the absolute stereochemistry of (+)-1 has been established by 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.Keywords
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