The Ever-Challenging Quassinoids

Claude Spino

doi:10.1055/s-2005-921930

ACCOUNT

The Ever-Challenging Quassinoids

Claude Spino*
Département de Chimie, Université de Sherbrooke, 2500 Boul. Université, Sherbrooke, QC, J1K 2R1, Canada
Fax: +1(819)8218017; e-Mail: Claude.Spino@USherbrooke.ca;

Abstract

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Abstract

The evolution of a synthetic approach to the challenging targets quassinoids is described.

1 Introduction

2 The Diels-Alder Reaction as a Key Feature

2.1 Intermolecular Diels-Alder

2.2 Intramolecular Diels-Alder

2.3 Unsuccessful Diels-Alder Cycloadditions

3 The Diene-Transmissive Approach to Quassinoids

3.1 Without the C10 Methyl Group

3.2 With the C10 Methyl Group

4 A Successful Sequence

5 Conclusion and Outlook

Key words

quassinoids - Simaroubacea - diene-transmissive Diels-Alder cycloaddition - vinylallenes - S_N2′ displacement

Full Text

References

For reviews on the isolation and biological activities of quassinoids, see:

<A NAME="RA39205ST-1A">1a</A> Guo Z. Vangapandu S. Sindelar RW. Walker LA. Sindelar RD. Curr. Med. Chem. 2005, 12: 173

<A NAME="RA39205ST-1B">1b</A> Okano M. Fukamiya N. Lee KH. Stud. Nat. Prod. Chem. 1990, 7: 369

<A NAME="RA39205ST-1C">1c</A> Polonsky J. J. Fortschr. Chem. Org. Naturst. 1973, 30: 101

<A NAME="RA39205ST-1D">1d</A> Polonsky J. J. Fortschr. Chem. Org. Naturst. 1985, 47: 221

<A NAME="RA39205ST-2A">2a</A> Valenta Z. Gray AH. Papadopoulos S. Podesva C. Tetrahedron Lett. 1960, 1: 25

<A NAME="RA39205ST-2B">2b</A> Valenta Z. Gray AH. Orr DE. Papadopoulos S. Podesva C. Tetrahedron 1962, 18: 1433

<A NAME="RA39205ST-3A">3a</A> Clark EP. J. Am. Chem. Soc. 1937, 59: 927

<A NAME="RA39205ST-3B">3b</A> Clark EP. J. Am. Chem. Soc. 1937, 59: 2511

For a review on the synthetic aspect of quassinoids see:

<A NAME="RA39205ST-4A">4a</A> Kawada K. Kim M. Watt DS. Org. Prep. Proced. Int. 1989, 21: 521

<A NAME="RA39205ST-4B">4b</A> Murae T. Sasaki M. Stud. Nat. Prod. Chem. 1992, 11: 71

Recent syntheses include:

<A NAME="RA39205ST-4C">4c</A> Walker DP. Grieco PA. J. Am. Chem. Soc. 1999, 121: 9891

<A NAME="RA39205ST-4D">4d</A> Grieco PA. Collins JL. Huffman JC. J. Org. Chem. 1998, 63: 9576

<A NAME="RA39205ST-4E">4e</A> Shing TKM. Jiang Q. J. Org. Chem. 2000, 65: 7059

<A NAME="RA39205ST-5A">5a</A> VanderRoest JM. Grieco PA. J. Org. Chem. 1996, 61: 5316

<A NAME="RA39205ST-5B">5b</A> Stojanac N. Valenta Z. Can. J. Chem. 1991, 69: 853

<A NAME="RA39205ST-5C">5c</A> Hirota H. Yokoyama A. Miyaji K. Nakamura T. Igarashi M. Takahashi T. J. Org. Chem. 1991, 56: 1119

<A NAME="RA39205ST-5D">5d</A> Kim M. Kawada K. Gross RS. Watt DS. J. Org. Chem. 1990, 55: 504

<A NAME="RA39205ST-5E">5e</A> For a relay synthesis see: Sasaki M. Murae T. Takahashi T. J. Org. Chem. 1990, 55: 528

For selected examples see:

<A NAME="RA39205ST-6A">6a</A> Alvarez-Manzaneda EJ. Romera JL. Barrero AF. Alvarez-Manzaneda R. Chahboun R. Meneses R. Aparicio M. Tetrahedron 2005, 61: 837

<A NAME="RA39205ST-6B">6b</A> Donahue MG. Hart DJ. Can. J. Chem. 2004, 82: 314

<A NAME="RA39205ST-6C">6c</A> Spino C. Hill B. Dubé P. Gingras S. Can. J. Chem. 2003, 81: 81

<A NAME="RA39205ST-6D">6d</A> Kraus GA. Cui W. J. Org. Chem. 2002, 67: 9475

<A NAME="RA39205ST-6E">6e</A> Barriault L. Ouellet SG. Deslongchamps P. Tetrahedron 1997, 53: 14937

<A NAME="RA39205ST-6F">6f</A> Takeya T. Motegi S. Itoh T. Tobinaga S. Chem. Pharm. Bull. 1997, 45: 613

<A NAME="RA39205ST-6G">6g</A> Govindan SV. Fuchs PL. J. Org. Chem. 1988, 53: 2593

<A NAME="RA39205ST-6H">6h</A> Kerwin SM. Paul AG. Heathcock CH. J. Org. Chem. 1987, 52: 1686

<A NAME="RA39205ST-6I">6i</A> Shishido K. Takahashi K. Fukumoto K. Kametani T. Honda T. J. Org. Chem. 1987, 52: 5704

<A NAME="RA39205ST-6J">6j</A> Stevens RV. Vinogradoff AP. J. Org. Chem. 1985, 50: 4056

<A NAME="RA39205ST-6K">6k</A> Ziegler FE. Klein SI. Pati UK. Wang TF. J. Am. Chem. Soc. 1985, 107: 2730

<A NAME="RA39205ST-6L">6l</A> Batt DG. Takamura N. Ganem B. J. Am. Chem. Soc. 1984, 106: 3353

<A NAME="RA39205ST-7A">7a</A> Wiseman CL. Yap HY. Bedikian AY. Bodey GP. Blumenschein GR. Am. J. Clin. Oncol. 1982, 5: 389

<A NAME="RA39205ST-7B">7b</A> Arsenau JC. Wolter JM. Kuperminc M. Ruckdeschel JC. Invest. New Drugs 1983, 1: 239

<A NAME="RA39205ST-8">8</A> Cuendet M. Pezzuto JM. J. Nat. Prod. 2004, 67: 269

<A NAME="RA39205ST-9A">9a</A> Polonsky J. Chemistry and Biological Activity of the Quassinoids, In The Chemistry and Chemical Taxonomy of the Rutales Waterman PG. Grandon MF. Academic Press; New York: 1983. p.247

<A NAME="RA39205ST-9B">9b</A> Lidert Z. Wing K. Polonsky J. Imakura Y. Okano M. Tani S. Lin Y.-M. Kiyokawa H. Lee K.-H. J. Nat. Prod. 1987, 50: 442

<A NAME="RA39205ST-9C">9c</A> Rahman S. Fukamiya N. Okano M. Tagahara K. Lee K.-H. Chem. Pharm. Bull. 1997, 45: 1527

<A NAME="RA39205ST-10A">10a</A> Grieco PA. Ferriño S. Vidari G. J. Am. Chem. Soc. 1980, 102: 7586

<A NAME="RA39205ST-10B">10b</A> Grieco PA. Vidari G. Ferriño S. Tetrahedron Lett. 1980, 21: 1619

For selected examples of other total syntheses by the Grieco group, see:

<A NAME="RA39205ST-10C">10c</A> Grieco PA. Lis R. Ferriño S. Law JY. J. Org. Chem. 1984, 49: 2342

<A NAME="RA39205ST-10D">10d</A> Grieco PA. Parker DT. Nargund RP. J. Am. Chem. Soc. 1988, 110: 5568

<A NAME="RA39205ST-10E">10e</A> Grieco PA. Collins JL. Moher ED. Fleck TJ. Gross RS. J. Am. Chem. Soc. 1993, 115: 6078

<A NAME="RA39205ST-10F">10f</A> Grieco PA. Collins JL. Huffman JC. J. Org. Chem. 1998, 63: 9576

<A NAME="RA39205ST-11">11</A> Weller DD. Stirchak EP. J. Org. Chem. 1983, 48: 4873

<A NAME="RA39205ST-12">12</A> Stevens RV. Angle SR. Kloc K. Mak KF. Trueblood KN. Liu Y.-X. J. Org. Chem. 1986, 51: 4347

<A NAME="RA39205ST-13A">13a</A> Kraus GA. Taschner MJ. Shimagaki M. J. Org. Chem. 1982, 47: 4271

<A NAME="RA39205ST-13B">13b</A> Kraus GA. Cui W. J. Org. Chem. 2002, 67: 9475

<A NAME="RA39205ST-14A">14a</A> Stojanac N. Stojanac Z. White P. Valenta Z. Can. J. Chem. 1979, 57: 3346

<A NAME="RA39205ST-14B">14b</A> Stojanac N. Sood A. Stojanac Z. Valenta Z. Can. J. Chem. 1975, 53: 619

<A NAME="RA39205ST-15">15</A> Kraus GA. Krolsky ME. J. Org. Chem. 1986, 51: 3347

<A NAME="RA39205ST-16A">16a</A> Shishido K. Takahashi K. Fukumoto K. J. Org. Chem. 1987, 52: 5704

<A NAME="RA39205ST-16B">16b</A> Shishido K. Saitoh T. Fukumoto K. Kametani T. J. Chem. Soc., Chem. Commun. 1983, 852

<A NAME="RA39205ST-17">17</A> Schlessinger RH. Wong J.-W. Poss MA. Springer JP. J. Org. Chem. 1985, 50: 3950

<A NAME="RA39205ST-18">18</A> Shing TKM. Jiang Q. Mak TCW. J. Org. Chem. 1998, 63: 2056

<A NAME="RA39205ST-19">19</A> Herscovici J. Delatre S. Boumaïza L. Antonakis K. J. Org. Chem. 1993, 58: 3928

<A NAME="RA39205ST-20">20</A> Mandell L. Lee DE. Courtney LF. J. Org. Chem. 1982, 47: 610

<A NAME="RA39205ST-21A">21a</A> Voyle M. Dunlap NK. Watt DS. J. Org. Chem. 1983, 48: 3242

<A NAME="RA39205ST-21B">21b</A> Voyle M. Kyler KS. Arseniyadis S. Dunlap NK. Watt DS. J. Org. Chem. 1983, 48: 470

<A NAME="RA39205ST-22A">22a</A> Blomquist AT. Verdol JA. J. Am. Chem. Soc. 1955, 77: 81

<A NAME="RA39205ST-22B">22b</A> Bailey WJ. Economy J. J. Am. Chem. Soc. 1955, 77: 1133

<A NAME="RA39205ST-22C">22c</A> Bailey WJ. Cunov CH. Nicholas L. J. Am. Chem. Soc. 1955, 77: 2787

<A NAME="RA39205ST-23A">23a</A> Tsuge O. Wada E. Kanemasa S. Chem. Lett. 1983, 239

<A NAME="RA39205ST-23B">23b</A> Tsuge O. Wada E. Kanemasa S. Sakoh H. Bull. Chem. Soc. Jpn. 1984, 57: 3221

<A NAME="RA39205ST-23C">23c</A> Tsuge O. Kanemasa S. Sakoh H. Wada E. Bull. Chem. Soc. Jpn. 1984, 57: 3234

<A NAME="RA39205ST-23D">23d</A> Wada E. Kanemasa S. Tsuge O. Bull. Chem. Soc. Jpn. 1989, 62: 1198

<A NAME="RA39205ST-23E">23e</A> Tsuge O. Hatta T. Yakata K. Maeda H. Chem. Lett. 1994, 1833

<A NAME="RA39205ST-23F">23f</A> Tsuge O. Hatta T. Yoshitomi H. Kurosaka K. Fujiwara T. Maeda H. Kakehi A. Heterocycles 1995, 41: 225

<A NAME="RA39205ST-23G">23g</A> Tsuge O. Hatta T. Fujiwara T. Yokohari T. Tsuge A. Heterocycles 1999, 50: 661

<A NAME="RA39205ST-23H">23h</A> Fallis AG. Parra S. Legoupy S. Woo S. Org. Lett. 1999, 1: 1013

<A NAME="RA39205ST-23I">23i</A> Fallis AG. Squire N. Woo S. Org. Lett. 1999, 1: 573

<A NAME="RA39205ST-24">24</A> Spino C. Liu G. J. Org. Chem. 1993, 58: 817

<A NAME="RA39205ST-25">25</A> Spino C. Beaulieu C. J. Am. Chem. Soc. 1998, 120: 11832

<A NAME="RA39205ST-26">26</A> Danishefsky S. Bednarski M. Tetrahedron Lett. 1984, 25: 721

<A NAME="RA39205ST-27">27</A> Spino C. Tu N. Liu G. Girard S. J. Org. Chem. 1994, 59: 5596

<A NAME="RA39205ST-28A">28a</A> Reich HJ. Eisenhart EK. Whipple WL. Kelly MJ. J. Am. Chem. Soc. 1988, 110: 6432 ; and references therein

<A NAME="RA39205ST-28B">28b</A> Spino C. Thibault C. Gingras S. J. Org. Chem. 1998, 63: 5283

<A NAME="RA39205ST-29">29</A> Sieburth SM. Lang J. J. Org. Chem. 1999, 64: 1780

<A NAME="RA39205ST-30">30</A> Dion A. Dubé P. Spino C. Org. Lett. 2005, in press