Asymmetric synthesis of alkaloid (−)-(2S,4S ) SS 20846 A and its C-4 epimer

Ripoche, Isabelle; Canet, Jean-Louis; Aboab, Bettina; Gelas, Jacques; Troin, Yves

doi:10.1039/a804288h

Cited by 14 publications

(16 citation statements)

References 28 publications

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“…10 This fact was demonstrated with 2-substituted-4-piperidones. 8 Confirmation that this phenomenon also occurred with the 2,6-cis-disubstituted piperidone 7 has been obtained by conformational analysis using the Batchmin program within the MM2 force field of the Macromodel package (Fig. 2).…”

Section: Resultsmentioning

confidence: 63%

A simple synthesis of (+)- and (−)-alkaloid 241D and C-4 epimers

Ciblat

Calinaud

Canet

et al. 2000

J. Chem. Soc., Perkin Trans. 1

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Section: Resultsmentioning

confidence: 63%

A simple synthesis of (+)- and (−)-alkaloid 241D and C-4 epimers

Ciblat

Calinaud

Canet

et al. 2000

J. Chem. Soc., Perkin Trans. 1

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“…In one study a 2-substituted NH 4-oxo piperidine with L-Selectride gave the cis-product (cis/trans = 90:10), while an N-protected derivative afforded the trans-isomer (cis/ trans = 5:95). 20 In another study a 2-substituted N-PMP-4-oxopiperidine gave a 89:11 cis/trans ratio of products with L-Selectride, and with NaBH 4 /CeCl 3 the ratio was reversed (cis/trans = 30:70). 21 On the other hand 2,6-disubstituted 4-oxo piperidines give the cis-and trans-products with NaBH 4 and L-Selectride, respectively.…”

Section: Figurementioning

confidence: 96%

Asymmetric Synthesis of the Four Stereoisomers of 4-Hydroxypipecolic Acid

Davis¹,

Fang²,

Chao³

et al. 2000

Synthesis

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The asymmetric synthesis of all four stereoisomers of 4-hydroxypipecolic acid (1) from the polyfunctionalized chiral building blocks d-amino b-keto esters (S S ,R)-(+)-5 or (R S ,S)-(-)-5 is described. Key steps in the synthesis are the stereoselective reductions of b-phenylpiperidine-2,4-dione (6) and N-sulfinyl d-amino b-keto esters 5 to cis 4-hydroxy 2-piperidinone 7 and syn-d-amino b-hydroxy ester 9, respectively. The only protecting/deprotecting group chemistry required is related to the oxidation step.

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“…Troin developed an unusual Mannich route to piperidines using chiral h 2 -butadiene iron complexes. 154 As shown in Scheme 59 condensation of amine 246 with chiral aldehyde 247 under acidic conditions yielded the piperidine iron complex 248 in 68%. The observed diastereoselectivity is probably due to an equilibrium between iminium ion conformers A and B.…”

Section: Scheme 57mentioning

confidence: 99%