N-tert-Butanesulfinyl Imines in Alkaloid
Synthesis: Stereoselective Synthesis of (R)-Coniine
and Formal Synthesis of (S)-δ-Coniceine

Kongara Damodar; Maram Lingaiah; Nisith Bhunia; Biswanath Das

doi:10.1055/s-0030-1260117

PAPER

N-tert-Butanesulfinyl Imines in Alkaloid Synthesis: Stereoselective Synthesis of (R)-Coniine and Formal Synthesis of (S)-δ-Coniceine [¹]

Kongara Damodar, Maram Lingaiah, Nisith Bhunia, Biswanath Das*
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: biswanathdas@yahoo.com;

Abstract

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Abstract

A stereoselective synthesis of the hemlock alkaloid (R)-coniine and a formal synthesis of the indolizidine alkaloid (S)-δ-coniceine were achieved by means of a highly diastereoselective Barbier-type indium-mediated allylation strategy involving (S)-(N-tert-butanesulfinyl)imines.

Key words

alkaloids - stereoselective synthesis - piperidines

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References

Part 49 in the series ‘Synthetic Studies on Natural Products’.

<A NAME="RZ39911SS-2A">2a</A> Strunz GM. Findlay JA. In The Alkaloids: Chemistry and Pharmacology Vol. 26: Brossi A. Academic Press; San Diego: 1986. p.89

<A NAME="RZ39911SS-2B">2b</A> Fodor GB. Colasanti B. In Alkaloids: Chemical and Biological Perspectives Vol. 3: Pelletier SW. Wiley; New York: 1986. p.1

For reviews on piperidine alkaloids, see:

<A NAME="RZ39911SS-3A">3a</A> Plunkett AO. Nat. Prod. Rep. 1994, 11: 581

<A NAME="RZ39911SS-3B">3b</A> Hammann P. In Organic Synthesis Highlights II Waldmann H. VCH; Weinheim: 1995. p.323

<A NAME="RZ39911SS-3C">3c</A> Schneider MJ. In Alkaloids: Chemical and Biological Perspectives Vol. 10: Pelletier SW. Wiley; New York: 1996. p.155

<A NAME="RZ39911SS-3D">3d</A> O’Hagan D. Nat. Prod. Rep. 2000, 17: 435

<A NAME="RZ39911SS-3E">3e</A> Bailey PD. Millwood PA. Smith PD. Chem. Commun. 1998, 633

For reviews on indolizidine alkaloids, see:

<A NAME="RZ39911SS-4A">4a</A> Takahata H. Momose T. In The Alkaloids: Chemistry and Pharmacology Vol. 44: Cordell GA. Academic Press; San Diego: 1993. p.189

<A NAME="RZ39911SS-4B">4b</A> Michael JP. Nat. Prod. Rep. 2008, 25: 139

<A NAME="RZ39911SS-5A">5a</A> Michael JP. Nat. Prod. Rep. 2007, 24: 191

<A NAME="RZ39911SS-5B">5b</A> Daly JW. Garraffo HM. Spande TF. J. Nat. Prod. 2005, 68: 1556

<A NAME="RZ39911SS-5C">5c</A> Daly JW. J. Med. Chem. 2003, 46: 445

<A NAME="RZ39911SS-6">6</A> Daly JW. Garraffo HM. Spande TF. In Alkaloids: Chemical and Biological Perspectives Vol. 13: Pelletier SW. Pergamon; Oxford: 1999. p.1

<A NAME="RZ39911SS-7A">7a</A> Reding MT. Buchwald SL. J. Org. Chem. 1998, 63: 6344

<A NAME="RZ39911SS-7B">7b</A> Wilkinson TJ. Stehle NW. Beak P. Org. Lett. 2000, 2: 155

<A NAME="RZ39911SS-7C">7c</A> Nukui S. Sodeoka M. Shibasaki M. Tetrahedron Lett. 1993, 34: 4965

<A NAME="RZ39911SS-7D">7d</A> Sato Y. Nukui S. Sodeoka M. Shibasaki M. Tetrahedron 1994, 50: 371

<A NAME="RZ39911SS-7E">7e</A> Takahata H. Kubota M. Takahashi S. Momose T. Tetrahedron: Asymmetry 1996, 7: 3047

<A NAME="RZ39911SS-7F">7f</A> Panchgalle SP. Bidwai HB. Chavan SP. Kalkote UR. Tetrahedron: Asymmetry 2010, 21: 2399

<A NAME="RZ39911SS-7G">7g</A> Coldham I. Leonori D. J. Org. Chem. 2010, 75: 4069

<A NAME="RZ39911SS-8A">8a</A> Enders D. Tiebes J. Liebigs Ann. Chem. 1993, 173

<A NAME="RZ39911SS-8B">8b</A> Oppolzer W. Pure Appl. Chem. 1994, 66: 2127

<A NAME="RZ39911SS-8C">8c</A> Munchhof MJ. Meyers AI. J. Org. Chem. 1995, 60: 7084

<A NAME="RZ39911SS-8D">8d</A> Kim Y. Choi J. Tetrahedron Lett. 1996, 37: 5543

<A NAME="RZ39911SS-8E">8e</A> Moody C. Lightfoot A. Gallagher P. J. Org. Chem. 1997, 62: 746

<A NAME="RZ39911SS-8F">8f</A> Pandey G. Das P. Tetrahedron Lett. 1997, 38: 9073

<A NAME="RZ39911SS-8G">8g</A> Yamazaki N. Kibayashi C. Tetrahedron Lett. 1997, 38: 4623

<A NAME="RZ39911SS-8H">8h</A> Katritzky A. Qiu G. Yang B. Steel P. J. Org. Chem. 1998, 63: 6699

<A NAME="RZ39911SS-8I">8i</A> Takahata H. Kubota M. Ikota N. J. Org. Chem. 1999, 64: 8594

<A NAME="RZ39911SS-8J">8j</A> Eskici M. Gallagher T. Synlett 2000, 1360

<A NAME="RZ39911SS-8K">8k</A> Bois F. Gardette D. Gramain JC. Tetrahedron Lett. 2000, 41: 8769

<A NAME="RZ39911SS-8L">8l</A> Pachamuthu K. Vankar YD. J. Organomet. Chem. 2001, 624: 359

<A NAME="RZ39911SS-8M">8m</A> Davis SB. McKervey MA. Tetrahedron Lett. 1999, 40: 1229

<A NAME="RZ39911SS-8N">8n</A> Yoda H. Katoh H. Ujihara Y. Takabe K. Tetrahedron Lett. 2001, 42: 2509

<A NAME="RZ39911SS-8O">8o</A> Hjelmgaard T. Gardette D. Tanner D. Aitken DJ. Tetrahedron: Asymmetry 2007, 18: 671

<A NAME="RZ39911SS-8P">8p</A> Costa A. Naejera C. Sansano JM. Tetrahedron: Asymmetry 2001, 12: 205

<A NAME="RZ39911SS-8Q">8q</A> Park SH. Kang HJ. Ko S. Park S. Chang S. Tetrahedron: Asymmetry 2001, 12: 2621

<A NAME="RZ39911SS-8R">8r</A> Groaning MD. Meyers AI. Chem. Commun. 2000, 1027

<A NAME="RZ39911SS-9">9</A> Serino C. Stehle N. Park YS. Florio S. Beak P. J. Org. Chem. 1999, 64: 1160

<A NAME="RZ39911SS-10">10</A> Sánchez-Sancho F. Herradón B. Tetrahedron: Asymmetry 1998, 9: 1951

<A NAME="RZ39911SS-11">11</A> Pilli RA. de Fátima Alves C. Böckelmann MA. Mascarentas YP. Nery JG. Vencato I. Tetrahedron Lett. 1999, 40: 2891

<A NAME="RZ39911SS-12">12</A> Robak MT. Herbage MA. Ellman JA. Chem. Rev. 2010, 110: 3600

<A NAME="RZ39911SS-13A">13a</A> Das B. Laxminarayana K. Krishnaiah M. Kumar DN. Bioorg. Med. Chem. Lett. 2009, 19: 6396

<A NAME="RZ39911SS-13B">13b</A> Das B. Suneel K. Satyalakshmi G. Kumar DN. Tetrahedron: Asymmetry 2009, 20: 1536

<A NAME="RZ39911SS-13C">13c</A> Das B. Kumar DN. Tetrahedron Lett. 2010, 51: 6011

<A NAME="RZ39911SS-14A">14a</A> Cogan DA. Ellman JA. J. Am. Chem. Soc. 1999, 121: 268

<A NAME="RZ39911SS-14B">14b</A> Liu G. Cogan DA. Owens TD. Tang TP. Ellman JA. J. Org. Chem. 1999, 64: 1278

<A NAME="RZ39911SS-15">15</A> Foubelo F. Yus M. Tetrahedron: Asymmetry 2004, 15: 3823

<A NAME="RZ39911SS-16">16</A> Wang B. Liu R.-H. Eur. J. Org. Chem. 2009, 2845

<A NAME="RZ39911SS-17">17</A> Plechiers M. Hootele C. Tetrahedron Lett. 1993, 34: 7569

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