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Stereospecific route to enantiopure all cis-2,3,6-trisubstituted piperidines. Facile synthesis of (−)-deoxocassine and (+)-azimic acid

✍ Scribed by Dawei Ma; Nan Ma

Book ID
104253573
Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
255 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Reduction of the enantiopure b-amino esters 10 provides the g-amnio alcohol 11, which is condensed with 2,4-pentadione to afford 12. Stepwise cyclization of 12 produced the cyclic enamine 13, which is hydrogenated to deliver all cis-2,3,6-trisubstituted piperidine 14. Using this reaction sequence and subsequent Baeyer-Villiger oxidation as the key step (-)-deoxocassine and (+)-azimic acid are synthesized.

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Synthesis of enantiomerically pure all c
Synthesis of enantiomerically pure all cis-2,3,6-trisubstituted piperidine: a silicon mediated total synthesis of (+)-carpamic acid
✍ Rekha Singh; Sunil K Ghosh 📂 Article 📅 2002 🏛 Elsevier Science 🌐 French ⚖ 259 KB

A stereoselective total synthesis of (+)-carpamic acid 1 has been achieved from the s-symmetric 3-[dimethyl(phenyl)silyl]glutaric anhydride 11 featuring its asymmetric desymmetrisation using oxazolidinone 12. The dimethyl(phenyl)silyl group is not only acting as a masked hydroxy group but also stere