Prolinamide/PPTS-Catalyzed Hajos-Parrish Annulation: Efficient Approach to the Tricyclic Core of Cylindricine-Type Alkaloids

Abstract

A series of Wieland-Miescher ketone analogues bearing highly functionalized substituents are efficiently constructed in high enantioselectivities and good yields using catalytic amounts of prolinamide and PPTS. We have successfully utilized this reaction as a key step to synthesize the tricyclic core of cylindricine type alkaloids.

prolinamide - Hajos-Parrish annulation - Wieland-Miescher ketone analogues - cylindricine type alkaloids - intramolecular Schmidt reaction

References and Notes

For recent instance, see:

<A NAME="RW09908ST-1A">1a</A> Kaliappan KP. Ravikumar V. Org. Lett.  2007,  9:  2417 

<A NAME="RW09908ST-1B">1b</A> Lanfranchi DA. Hanquet G. J. Org. Chem.  2006,  71:  4854 

<A NAME="RW09908ST-1C">1c</A> González SA. Bradshaw BJ. Bonjoch CJ. J. Org. Chem.  2005,  70:  3749 

<A NAME="RW09908ST-1D">1d</A> Hagiwara H. Hamano K. Nozawa M. Hoshi T. Suzuki T. Kido F. J. Org. Chem.  2005,  70:  2250 

<A NAME="RW09908ST-1E">1e</A> Shigehisa H. Mizutani T. Tosaki S. Ohshima T. Shibasaki M. Tetrahedron  2005,  61:  5057 

<A NAME="RW09908ST-1F">1f</A> Kanoh N. Smith ABIII. Ishiyama H. Minakawa N. Rainier JD. Hartz RA. Cho YS. Cui H. Moser WH. J. Am. Chem. Soc.  2003,  125:  8228 

<A NAME="RW09908ST-1G">1g</A> Suzuki A. Nakatani M. Nakamura M. Kawaguchi K. Inoue M. Katoh T. Synlett  2003,  329 

<A NAME="RW09908ST-1H">1h</A> Deng W.-P. Zhong M. Guo X.-C. Kende AS. J. Org. Chem.  2003,  68:  7422 

<A NAME="RW09908ST-1I">1i</A> Ling T. Chowdhury C. Kramer BA. Vong BG. Palladino MA. Theodorakis EA. J. Org. Chem.  2001,  66:  8843 

<A NAME="RW09908ST-2A">2a</A> Wieland P. Miescher K. Helv. Chim. Acta  1950,  33:  2215 

<A NAME="RW09908ST-2B">2b</A> Hajos ZG. Parrish DR. J. Org. Chem.  1974,  39:  1615 

<A NAME="RW09908ST-2C">2c</A> Eder U. Sauer G. Wiechert R. Angew. Chem., Int. Ed. Engl.  1971,  10:  496 

<A NAME="RW09908ST-3A">3a</A> Davies SG. Russell AJ. Sheppard RL. Smith AD. Thomson JE. Org. Biomol. Chem.  2007,  5:  3190 

<A NAME="RW09908ST-3B">3b</A> He L. Hecheng Huaxue  2007,  15:  231 

<A NAME="RW09908ST-3C">3c</A> Sulzer-Mossé S. Laars M. Kriis K. Kanger T. Alexakis A. Synthesis  2007,  1729 

<A NAME="RW09908ST-3D">3d</A> Kanger T. Kriis K. Laars M. Kailas T. Müürisepp A.-M. Pehk T. Lopp M. J. Org. Chem.  2007,  72:  5168 

<A NAME="RW09908ST-3E">3e</A> Lacoste E. Vaique E. Berlande M. Pianet I. Vincent J.-M. Landais Y. Eur. J. Org. Chem.  2007,  167 

<A NAME="RW09908ST-3F">3f</A> Nagamine T. Inomata K. Endo Y. Paquette LA. J. Org. Chem.  2007,  72:  123 

<A NAME="RW09908ST-3G">3g</A> Kriis K. Kanger T. Laars M. Kailas T. Müürisepp A.-M. Pehk T. Lopp M. Synlett  2006,  1699 

<A NAME="RW09908ST-3H">3h</A> Kasai Y. Shimanuki K. Kuwahara S. Watanabe M. Harada N. Chirality  2006,  18:  177 

<A NAME="RW09908ST-3I">3i</A> Davies SG. Sheppard RL. Smith AD. Thomson JE. Chem. Commun.  2005,  3802 

<A NAME="RW09908ST-3J">3j</A> Cheong PH. Houk KN. Warrier JS. Hanessian S. Adv. Synth. Catal.  2004,  346:  1111 

<A NAME="RW09908ST-3K">3k</A> Fuhshuku K.-I. Tomita M. Sugai T. Adv. Synth. Catal.  2003,  345:  766 

<A NAME="RW09908ST-3L">3l</A> Lo L.-C. Shie J.-J. Chou T.-C. J. Org. Chem.  2002,  67:  282 

<A NAME="RW09908ST-3M">3m</A> Hioki H. Hashimoto T. Kodama M. Tetrahedron: Asymmetry  2000,  11:  829 

<A NAME="RW09908ST-3N">3n</A> Fuhshuku K.-I. Funa N. Akeboshi T. Ohta H. Hosomi H. Ohba S. Sugai T. J. Org. Chem.  2000,  65:  129 

<A NAME="RW09908ST-3O">3o</A> Bui T. Barbas CF. Tetrahedron Lett.  2000,  41:  6951 

<A NAME="RW09908ST-4">4</A> Gu P. Zhao Y.-M. Tu YQ. Ma Y. Zhang F. Org. Lett.  2006,  8:  5271 

<A NAME="RW09908ST-5A">5a</A> Hiroya K. Takahashi T. Shimomae K. Sakamoto T. Chem. Pharm. Bull.  2005,  53:  207 

<A NAME="RW09908ST-5B">5b</A> Ziegler FE. Wallace OB. J. Org. Chem.  1995,  60:  3626 

<A NAME="RW09908ST-6">6</A> Ramachary DB. Kishor M. J. Org. Chem.  2007,  72:  5056 

<A NAME="RW09908ST-7A">7a</A> Inomata K. Barrague M. Paquette LA. J. Org. Chem.  2005,  70:  533 

<A NAME="RW09908ST-7B">7b</A> Hanselmann R. Benn M. Synth. Commun.  1996,  26:  945 

For very recent instance of prolinamide catalytic aldol reaction, see:

<A NAME="RW09908ST-8A">8a</A> Guillena G. Hita M. Nájera C. Viózquez SF. Tetrahedron: Asymmetry  2007,  18:  2300 

<A NAME="RW09908ST-8B">8b</A> Russo A. Botta G. Lattanzi A. Tetrahedron  2007,  63:  11886 

<A NAME="RW09908ST-8C">8c</A> Tang Z. Marx A. Angew. Chem. Int. Ed.  2007,  46:  7297 

<A NAME="RW09908ST-8D">8d</A> Hong B. Wu M. Tseng H. Huang G. Su C. Liao J. J. Org. Chem.  2007,  72:  8459 

<A NAME="RW09908ST-8E">8e</A> Peng Y. Liu H. Cui M. Cheng J. Chin. J. Chem.  2007,  25:  962 

<A NAME="RW09908ST-8F">8f</A> Dodda R. Zhao C. Synlett  2007,  1605 

<A NAME="RW09908ST-8G">8g</A> Guillena G. Hita MC. Nájera C. Tetrahedron: Asymmetry  2007,  18:  1272 

<A NAME="RW09908ST-8H">8h</A> Aratake S. Itoh T. Okano T. Usui T. Shoji M. Hayashi Y. Chem. Commun.  2007,  2524 

<A NAME="RW09908ST-8I">8i</A> Zhang F. Peng Y. Liao S. Gong Y. Tetrahedron  2007,  63:  4636 

<A NAME="RW09908ST-8J">8j</A> Ma G. Zhang Y. Shi M. Synthesis  2007,  197 

<A NAME="RW09908ST-9">9</A> Hayashi Y. Yamaguchi J. Hibino K. Sumiya T. Urushima T. Shoji M. Hashizume D. Koshino H. Adv. Synth. Catal.  2004,  346:  1435 

<A NAME="RW09908ST-10A">10a</A> Tang Z. Cun L.-F. Cui X. Mi A.-Q. Jiang Y.-Z. Gong L.-Z. Org. Lett.  2006,  8:  1263 

<A NAME="RW09908ST-10B">10b</A> Cobb AJA. Shaw DM. Longbottom DA. Gold JB. Ley SV. Org. Biomol. Chem.  2005,  3:  84 

<A NAME="RW09908ST-10C">10c</A> Berkessel A. Koch B. Lex J. Adv. Synth. Catal.  2004,  346:  1141 

<A NAME="RW09908ST-11">11</A> Rajamannar T. Balasubramanian KK. Synth. Commun.  1994,  24:  279 

<A NAME="RW09908ST-12A">12a</A> Blackman AJ. Li C. Hockless DCR. Skelton BW. White AH. Tetrahedron  1993,  49:  8645 

<A NAME="RW09908ST-12B">12b</A> Li C. Blackman AJ. Aust. J. Chem.  1994,  47:  1355 

<A NAME="RW09908ST-12C">12c</A> Li C. Blackman AJ. Aust. J. Chem.  1995,  48:  955 

<A NAME="RW09908ST-13A">13a</A> Biard JF. Guyot S. Roussakis C. Verbist JF. Vercauteren J. Weber JF. Boukef K. Tetrahedron Lett.  1994,  35:  2691 

<A NAME="RW09908ST-13B">13b</A> Juge M. Grimaud N. Biard JF. Sauviat MP. Nabil M. Verbist JF. Petit JY. Toxicon  2001,  39:  1231 

<A NAME="RW09908ST-13C">13c</A> Sauviat MP. Vercauteren J. Grimaud N. Juge M. Nabil M. Petit JY. Biard JF.
J. Nat. Prod.  2006,  69:  558 

For a review and some recent work on the total synthesis of cylindricines and lepadiformine, see:

<A NAME="RW09908ST-14A">14a</A> Weinreb SM. Chem. Rev.  2006,  106:  2531 

<A NAME="RW09908ST-14B">14b</A> Caldwell JJ. Craig D. Angew. Chem. Int. Ed.  2007,  119:  2685 

<A NAME="RW09908ST-14C">14c</A> Flick AC. Caballero MJA. Padwa A. Org. Lett.  2008,  10:  1871 

<A NAME="RW09908ST-15A">15a</A> Aubé J. Milligan GL. J. Am. Chem. Soc.  1991,  113:  8965 

<A NAME="RW09908ST-15B">15b</A> Milligan GL. Mossman CJ. Aubé J. J. Am. Chem. Soc.  1995,  117:  10449 

<A NAME="RW09908ST-15C">15c</A> Iyengar R. Schildknegt K. Aubé J. Org. Lett.  2000,  2:  1625 

<A NAME="RW09908ST-16">16</A>

See ref. 3e; we had increased the yield to 65% over two steps by using H₂O-AcOH (100:1.5) as the solvent and 2 equiv of MVK under reflux conditions in the second step.

<A NAME="RW09908ST-17A">17a</A> Kabalka GW. Yu S. Li NS. Tetrahedron Lett.  1997,  38:  5455 

<A NAME="RW09908ST-17B">17b</A> Kabalka GW. Yu S. Li NS. Can. J. Chem.  1998,  76:  800 

<A NAME="RW09908ST-18">18</A> Greene TW. Wuts PGM. Protective Groups in Organic Synthesis   3rd ed.:  Wiley; New York: 1999.  Chap. 4.

<A NAME="RW09908ST-19">19</A> Thomsen I. Clausen K. Scheibye S. Lawesson S.-O. Org. Synth.  1984,  62:  158 

<A NAME="RW09908ST-20">20</A>

CCDC 696349 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.