期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 70, 期 15, 页码 5954-5963出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo050529k
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资金
- NINDS NIH HHS [R01 NS020036, NS 20036] Funding Source: Medline
A series of 6.5.5 spiro bicyclic lactam scaffolds were synthesized from pipecolic acid in a sequence of reactions that was initiated with the alpha-allylation of tert-butoxycarbonyl pipecolic acid. Oxidative cleavage of the olefin to give an aldehyde followed by condensation with D-cysteine methyl ester gave a mixture of pipecolyl thiazolidines. Cyclization of the pipecolyl thiazolidines with Mukaiyama's reagent yielded the spiro bicyclic lactams 4a-d. Epimerization of the 7'a bridgehead carbon under acidic conditions was observed for those spiro bicyclic lactam scaffolds with an S stereochemistry at this position. The 6.5.5 spiro bicyclic lactam scaffold with the 3'S,6'R,7'aR stereochemistry mimicked a type H P-turn, while the scaffold with the 3'S,6'S,7'aR stereochemistry mimicked a right-handed poly-D-proline H helix.
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