Intramolecular [4+2]-Cycloaddition
of 5-Amino-Substituted Oxazoles as an Approach toward the Left-Hand
Segment of Haplophytine

Majid Chughtai; James M. Eagan; Albert Padwa

doi:10.1055/s-0030-1259302

LETTER

Intramolecular [4+2]-Cycloaddition of 5-Amino-Substituted Oxazoles as an Approach toward the Left-Hand Segment of Haplophytine

Majid Chughtai, James M. Eagan, Albert Padwa*
Department of Chemistry, Emory University, Atlanta, GA 30322, USA
Fax: +1(404)7276629; e-Mail: chemap@emory.edu;

Abstract

All articles of this category

Abstract

The [4+2]-cycloaddition chemistry of several 5-amino-substituted oxazoles has been examined as an approach toward the construction of the left-half segment of the aspidosperma alkaloid haplophytine.

Key words

5-aminooxazoles - intramolecular - Diels-Alder reaction - pyridines - haplophytine

Full Text

References

<A NAME="RG26310ST-1A">1a</A> Weinreb SM. Chem. Rev. 2006, 106: 2531

<A NAME="RG26310ST-1B">1b</A> Jeong JH. Weinreb SM. Org. Lett. 2006, 8: 2309

<A NAME="RG26310ST-2A">2a</A> Weingarten MD. Prein M. Price AT. Snyder JP. Padwa A. J. Org. Chem. 1997, 62: 2001

<A NAME="RG26310ST-2B">2b</A> Padwa A. Lynch SM. Mejiá-Oneto JM. Zhang H. J. Org. Chem. 2005, 70: 2206

<A NAME="RG26310ST-2C">2c</A> Meijá-Oneto JM. Padwa A. Tetrahedron Lett. 2004, 45: 9115

<A NAME="RG26310ST-3A">3a</A> Padwa A. Dimitroff M. Waterson AG. Wu T. J. Org. Chem. 1997, 62: 4088

<A NAME="RG26310ST-3B">3b</A> Padwa A. Wang Q.
J. Org. Chem. 2006, 71: 7391

<A NAME="RG26310ST-3C">3c</A> Zhang H. Padwa A. Org. Lett. 2006, 8: 247

<A NAME="RG26310ST-3D">3d</A> Zhang H. Boonsombat J. Padwa A. Org. Lett. 2007, 9: 279

<A NAME="RG26310ST-4A">4a</A> Mejiá-Oneto JM. Padwa A. Org. Lett. 2004, 6: 3241

<A NAME="RG26310ST-4B">4b</A> Padwa A. Lynch SM. Mejiá-Oneto JM. Zhang H. J. Org. Chem. 2005, 70: 2206

<A NAME="RG26310ST-4C">4c</A> Irgolic KJ. In Houben-Weyl 4th ed., Vol. E12b: Klamann D. Thieme; Stuttgart: 1990. p.150

<A NAME="RG26310ST-5">5</A> Saxton JE. in The Aldaloids: Chemistry and Biology Vol. 51: Cordell GA. Academic Press; San Diego / CA: 1998. p.1-197

<A NAME="RG26310ST-6">6</A> Yates P. MacLachlan FN. Rae ID. Rosenberger M. Szabo AG. Willis CR. Cava MP. Behforouz M. Lakshimikantham MV. Ziegler W. J. Am. Chem. Soc. 1973, 95: 7842

<A NAME="RG26310ST-7A">7a</A> He F. Bo Y. Altom JD. Corey EJ. J. Am. Chem. Soc. 1999, 121: 6771

<A NAME="RG26310ST-7B">7b</A> Sumi S. Matsumoto K. Tokuyama H. Fukuyama T. Org. Lett. 2003, 5: 1891

<A NAME="RG26310ST-7C">7c</A> Sumi S. Matsumoto K. Tokuyama H. Fukuyama T. Tetrahedron 2003, 59: 8571

<A NAME="RG26310ST-7D">7d</A> Marino JP. Cao G. Tetrahedron Lett. 2006, 47: 7711

<A NAME="RG26310ST-7E">7e</A> Nicolaou KC. Dalby SM. Majumder U. J. Am. Chem. Soc. 2008, 130: 14942

<A NAME="RG26310ST-8">8</A> Mejiá-Oneto JM. Padwa A. Org. Lett. 2006, 8: 3275

<A NAME="RG26310ST-9">9</A> Ueda H. Satoh H. Matsumoto K. Sugimoto K. Fukuyama T. Tokuyama H. Angew Chem. Int. Ed. 2009, 48: 7736

<A NAME="RG26310ST-10">10</A> Nicolaou KC. Dalby SM. Li S. Suzuki T. Chen DY.-K. Angew Chem. Int. Ed. 2009, 48: 7616

<A NAME="RG26310ST-11A">11a</A> Matsumoto K. Tokuyama H. Fukyama T. Synlett 2007, 3137

<A NAME="RG26310ST-11B">11b</A> Nicolaou KC. Majumder U. Roche SP. Chen DY.-K. Angew Chem. Int. Ed. 2007, 46: 4715

<A NAME="RG26310ST-12">12</A> For a review on bimolecular oxazole Diels-Alder reactions, see: Levin JI. Laakso LM. The Chemistry of Heterocyclic Compounds Vol. 60, Part A: Palmer DC. John Wiley and Sons; Hoboken / NJ: 2003. p.417-472

<A NAME="RG26310ST-13A">13a</A> Kondratèva GY. Khim. Nauka Prom. 1957, 2: 666 ; Chem. Abstr. 1958, 52, 6345a

<A NAME="RG26310ST-13B">13b</A> Kondratèva GY. Izv. Akad. Nauk SSSR., Otd. Khim. Nauk 1959, 484 ; Chem. Abstr. 1959, 53, 21940d

For some leading references, see:

<A NAME="RG26310ST-14A">14a</A> Jacobi PA. Advances in Heterocyclic Natural Product Synthesis Vol. 2: Pearson WH. JAI Press; Greenwich / CT: 1992. p.251-299

<A NAME="RG26310ST-14B">14b</A> Levin JI. Weinreb SM. J. Am. Chem. Soc. 1983, 105: 1397

<A NAME="RG26310ST-14C">14c</A> Levin JI. Weinreb SM. J. Org. Chem. 1984, 49: 4325

<A NAME="RG26310ST-14D">14d</A> Subramanyam C. Noguchi M. Weinreb SM. J. Org. Chem. 1989, 54: 5580

For some examples of intramolecular oxazole-olefin Diels-Alder reactions, see:

<A NAME="RG26310ST-15A">15a</A> Shimada S. Tojo T. Chem. Pharm. Bull. 1983, 31: 4247

<A NAME="RG26310ST-15B">15b</A> Levin JI. Tetrahedron Lett. 1989, 30: 2355

<A NAME="RG26310ST-15C">15c</A> Subramanyam C. Noguchi M. Weinreb SM. J. Org. Chem. 1989, 54: 5580

<A NAME="RG26310ST-15D">15d</A> Jung ME. Dansereau SMK. Heterocycles 1994, 39: 767

<A NAME="RG26310ST-15E">15e</A> Padwa A. Brodney MA. Liu B. Satake K. Wu T. J. Org. Chem. 1999, 64: 3595

<A NAME="RG26310ST-15F">15f</A> Sun X. Janvier P. Zhao G. Bienaymé H. Zhu J. Org. Lett. 2001, 3: 877

<A NAME="RG26310ST-15G">15g</A> Janvier P. Sun X. Bienaymé H. Zhu J. J. Am. Chem. Soc. 2002, 124: 2560

<A NAME="RG26310ST-15H">15h</A> González-Zamora E. Fayol A. Bois-Choussy M. Chiaroni A. Zhu J. Chem. Commun. 2001, 1684

<A NAME="RG26310ST-15I">15i</A> Gámez-Montano R. González-Zamora E. Potier P. Zhu J. Tetrahedron 2002, 58: 6351

<A NAME="RG26310ST-16A">16a</A> Clerin D. Kille G. Fleury JP. Tetrahedron 1974, 30: 469

<A NAME="RG26310ST-16B">16b</A> Clerin D. Fleury JP. Bull. Soc. Chim. Fr. 1973, 3127

<A NAME="RG26310ST-17">17</A> Lipshutz BH. Hungate RW. McCarthy KE. J. Am. Chem. Soc. 1983, 105: 7703

Supplementary Material

Supporting Information