- Rapid access to trans-2,6-disubstituted piperidines: Expedient total syntheses of (-)-solenopsin A and (+)-epi-dihydropinidine
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Expedient syntheses of (-)-solenopsin A and (+)-epi-dihydropinidine are reported, the key step in both being the one-pot multicomponent aza-silyl-Prins condensation reaction to yield a trans dihydropyridine. Georg Thieme Verlag Stuttgart.
- Dobbs, Adrian P.,Guesné, Sebastien J. J.
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p. 2101 - 2103
(2007/10/03)
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- Synthesis of trans-2,6-Dialkylpiperidines by Intramolecular Amidomercuriation and by 1,3-Cycloaddition of Alkenes to 2-Methyl-2,3,4,5-tetrahydropyridine Oxide
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Intramolecular amidomercuriation of methyl N-hept-6-en-2-ylcarbamate and reaction of the resulting organomercurial with sodium borohydride in the presence of acrylonitrile or dec-1-en-3-one has been used to prepare trans-2,6-dialkylpiperidines.A more stereoselective route lies in the cycloaddition of alkenes to 2-alkyl-2,3,4,5-tetrahydropyridine oxides followed by reductive cleavage of the resulting perhydroisoxazolopyridine.Both procedures are illustrated by synthesis of the fire ant-venom alkaloid, solenopsin A.
- Adams, David R.,Carruthers, William,Williams, Michael J.,Crowley, Patrick J.
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p. 1507 - 1513
(2007/10/02)
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- IMINE-EPOXIDE REARRANGEMENTS IN THE FORMATION OF SUBSTITUTED PIPERIDINES. A STEREOSELECTIVE SYNTHESIS OF (+-)SOLENOPSIN-A.
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The imine-epoxide rearrangement, followed by hydride reduction has been used to prepare substituted piperidine derivatives with control of stereochemistry.An application to the synthesis of (+-) solenopsin A is reported.
- Wasserman, Harry H.,Rusiecki, Victoria
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p. 4977 - 4980
(2007/10/02)
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- 2-CYANO Δ3 PIPERIDINES VI: A GENERAL METHOD FOR THE STEREOSELECTIVE SYNTHESIS OF CIS AND TRANS 2,6-DIALKYLPIPERIDINE ALKALOIDS
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The cis 2,6-dialkylpiperidine alkaloid (+/-) dihydro-pinidine 7b and the trans alkaloid (+/-) solenopsin A 5a were synthesized from a common α-aminonitrile synthon 1.The key step in this synthesis was the stereoselective reductive decyanation of the 1-benzyl-2-cyano-2',6-dialkylpiperidines 3a and 3b.
- Bonin, Martine,Romero, Jose R.,Grierson, David S.,Husson, Henri-Philippe
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p. 3369 - 3372
(2007/10/02)
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