Formal Synthesis of (+)-α-Conhydrine and Stereoselective Synthesis of Pyrrolidine Analogue via the Diastereoselective Chelation-Controlled Hydride Reduction and Wittig Reaction

REFERENCES

• (a) Casiraghi , G. ; Zanardi , F. ; Rassu , G. ; Spanu , P. Stereoselective approaches to bioactive carbohydrates and alkaloids, with a focus on recent syntheses drawing from the chiral pool . Chem. Rev. 1995 , 95 , 1677 – 1716 ; (b) Michael , J. P. Indolizidine and quinolizidine alkaloids . Nat. Prod. Rep. 1997 , 14 , 619 – 636 .
   Web of Science ®Google Scholar
• Wertheim , T. Ueber ein neues Alkaloïd in Conium maculatum . Justus Liebigs Ann. Chem. 1856 , 100 , 328 – 339 .
   Google Scholar
• Späth , E. ; Adler , E. Zur Konstitution des Konhydrins . Monatsh. Chem. 1933 , 63 , 127 – 140 .
   Google Scholar
• (a) Dong , G. R. ; Hong , S. ; Kim , S. I. ; Kim , I. S. ; Jung , Y. H. Stereoselective synthesis of (−)-α-conhydrine and its pyrrolidine analogue . Eur. J. Org. Chem. 2012 , 4200 – 4205 ; (b) Reyes , E. ; Ruiz , N. ; Vicario , J. L. ; Badia , D. ; Carrillo , L. Stereoselective total synthesis of (−)-β-conhydrine and (+)-α-conhydrine . Synthesis 2011 , 443 – 450 ; (c) Kamal , A. ; Vangala , S. R. An expedient total synthesis of optically active piperidine and indolizidine alkaloids (−)-β-conhydrine and (−)-lentiginosine . Tetrahedron 2011 , 67 , 1341 – 1347 ; (d) Bandini , E. ; Corda , G. ; D'Aurizio , A. ; Panunzio , M. A. Straightforward synthesis of conhydrine by hetero Diels–Alder strategy mediated by microwaves . Tetrahedron Lett. 2010 , 51 , 933 – 934 ; (e) Srivastava , A. K. ; Das , S. K. ; Panda , G. An approach towards the total synthesis of (+)-epiquinamide and (+)-α-conhydrine from Garner aldehyde . Tetrahedron 2009 , 65 , 5322 – 5327 ; (f) Pandey , S. K. ; Kumar , P. Stereoselective syntheses of (+)-α- and (−)-β-conhydrine from L-aspartic acid . Tetrahedron Lett. 2005 , 46 , 4091 – 4093 .
   Web of Science ®Google Scholar
• (a) Louvel , J. ; Chemla , F. ; Demont , E. ; Ferreira , F. ; Pérez-Luna , A. ; Voituriez , A. Stereoselective synthesis of syn-β-amino propargylic ethers: Application to the asymmetric syntheses of (+)-β-conhydrine and (−)-balanol . Adv. Synth. Catal. 2011 , 353 , 2137 – 2151 ; (b) Lebrun , S. ; Couture , A. ; Deniau , E. ; Grandclaudon , P. Asymmetric synthesis of the optically active piperidine alkaloid (+)-β-conhydrine . Tetrahedron: Asymmetry 2008 , 19 , 1245 – 1249 ; (c) Voituriez , A. ; Ferreira , F. ; Chemla , F. Short and efficient asymmetric synthesis of (−)-α-conhydrine . J. Org. Chem. 2007 , 72 , 5358 – 5361 ; (d) Jamieson , A. G. ; Sutherland , A. Ether-directed, stereoselective aza-Claisen rearrangements: Synthesis of the piperidine alkaloid, α-conhydrine . Org. Lett. 2007 , 9 , 1609 – 1611 ; (e) Chang , M.-Y. ; Kung , Y.-H. ; Chen , S.-T. Synthesis of α-conhydrine . Tetrahedron 2006 , 62 , 10843 – 10848 ; (f) Kandula , S. V. ; Kumar , P. Enantioselective synthesis of (−)-α-conhydrine via cyclic sulfate methodology . Tetrahedron Lett. 2003 , 44 , 1957 – 1958 .
   Web of Science ®Google Scholar
• Shaikh , T. M. ; Sudalai , A. Enantioselective synthesis of (+)-α-conhydrine and (−)-sedamine by L-proline-catalysed α-aminooxylation . Eur. J. Org. Chem. 2010 , 3437 – 3444 .
   Web of Science ®Google Scholar
• (a) Jin , T. ; Mu , Y. ; Kim , G. W. ; Kim , S. S. ; Kim , J. S. ; Huh , S. I. ; Lee , K. Y. ; Joo , J. E. ; Ham , W. H. Stereoselective synthesis of piperidine alkaloid (+)-α-conhydrine and its pyrrolidine analogue. Asian J. Org. Chem. 2012, 1, 232–237; (b) Mu , Y. ; Jin , T. ; Kim , G. W. ; Kim , J. S. ; Kim , S. S. ; Tian , Y. S. ; Oh , C. Y. ; Ham , W. H. Total syntheses of D-xylo- and D-arabino-phytosphingosine based on the syntheses of chiral 1,3-oxazines. Eur. J. Org. Chem. 2012, 2614–2620; (c) Mu , Y. ; Kim , J. Y. ; Jin , X. ; Park , S. H. ; Joo , J. E. ; Ham , W. H. Total synthesis of D-lyxo-phytosphingosine and formal synthesis of pachastrissamine via a chiral 1,3-oxazine. Synthesis 2012, 2340–2346; (d) Kim , J. Y. ; Mu , Y. ; Jin , X. ; Park , S. H. ; Pham , V. T. ; Song , D. K. ; Lee , K. Y. ; Ham , W. H. Efficient and stereoselective syntheses of DAB-1 and D-fagomine via chiral 1,3-oxazine. Tetrahedron 2011, 67, 9426–9432; (e) Pham , V. T. ; Joo , J. E. ; Lee , K. Y. ; Kim , T. W. ; Mu , Y. ; Ham , W. H. Stereoselective intramolecular cyclization of γ-allylbenzamide via π-allylpalladium complex catalyzed by Pd (0). Tetrahedron 2010, 66, 2123–2131.
   Web of Science ®Google Scholar
• (a) Hoffman , R. V. ; Maslouh , N. ; Cervantes-Lee , F. Highly stereoselective syntheses of syn- and anti-1,2-amino alcohols . J. Org. Chem. 2002 , 67 , 1045 – 1056 ; (b) Yamagishi , T. ; Muronoi , S. ; Hikishima , S. ; Shimeno , H. ; Soeda , S. ; Yokomatsu , T. Diastereoselective synthesis of γ-amino-δ-hydroxy-α,α-difluorophosphonates: A vehicle for structure–activity relationship studies on SMA-7, a potent sphingomyelinase inhibitor . J. Org. Chem. 2009 , 74 , 6350 – 6353 .
   PubMed Web of Science ®Google Scholar
• (a) Commandeur , M. ; Commandeur , C. ; Cossy , J. Synthesis of a platform to access bistramides and their analogues . Org. Lett. 2011 , 13 , 6018 – 6021 ; (b) Lebar , M. D. ; Baker , B. J. Synthesis of the C3–14 fragment of palmerolide A using a chiral pool–based strategy . Tetrahedron 2010 , 66 , 1557 – 1562 ; (c) Reddipalli , G. ; Venkataiah , M. ; Mishra , M. K. ; Fadnavis , N. W. Stereoselective synthesis of 2-epi-jaspine B via base-catalyzed intramolecular oxy-Michael conjugate addition approach . Tetrahedron: Asymmetry 2009 , 20 , 1802 – 1805 ; (d) Fernandes , R. A. ; Ingle , A. B. ; Chavan , V. P. Synthesis of β,γ-disubstituted-γ-lactones through a Johnson–Claisen rearrangement: A short route to xylobovide, nor-canadensolide, canadensolide, sporothriolide, and santolinolide . Tetrahedron: Asymmetry 2009 , 20 , 2835 – 2844 .
   PubMed Web of Science ®Google Scholar
• Roy , S. ; Sharma , A. ; Mula , S. ; Chattopadhyay , S. Metal-dependent reaction tuning with cyclopentylmetal reagents: Application to the asymmetric synthesis of (+)-α-conhydrine and (S)-2-cyclopentyl-2-phenylglycolic acid . Chem. Eur. J. 2009 , 15 , 1713 – 1722 .
   PubMed Web of Science ®Google Scholar
• (a) Kim , I. S. ; Oh , J. S. ; Zee , O. P. ; Jung , Y. H. Synthesis and conformational analysis of 3-hydroxypipecolic acid analogs via CSI-mediated stereoselective amination . Tetrahedron 2007 , 63 , 2622 – 2633 ; (b) Taniguchi , T. ; Ogasawara , K. A Diastereocontrolled synthesis of (+)-febrifugine: A potent antimalarial piperidine alkaloid . Org. Lett. 2000 , 2 , 3193 – 3195 .
   Web of Science ®Google Scholar