Diversity-Oriented Synthesis of Aminocyclohexitols from Garner’s Aldehyde

Abstract

A short and efficient synthetic route to three stereoisomeric aminocyclohexane tetrols of the quercitol type has been developed from l-serine, which featured stereoselective allylation, stereocontrolled dihydroxylation, and ring-closing metathesis as key steps.

Key words

allylation - carbocycles - dihydroxylation - metathesis - stereoselective synthesis

• References

• 1a Duchek J, Adams DR, Hudlicky T. Chem. Rev. 2011; 111: 4223
• 1b Arjona O, Gomez AM, Lopez JC, Plumet J. Chem. Rev. 2007; 107: 1919
• 1c Plumet J, Gomez AM, Lopez JC. Mini-Rev. Org. Chem. 2007; 4: 201
• 1d Shan M, O’Doherty GA. Synthesis 2008; 3171
• 1e Ogawa S In Carbohydrate Mimics: Concepts and Methods . Chapleur Y. Wiley-VCH; Weinheim: 1998: 87-106
• 2a Delgado A. Eur. J. Org. Chem. 2008; 3893
• 2b Diaz L, Delgado A. Curr. Med. Chem. 2010; 17: 2393
• 2c Ogawa S, Kanto M. Curr. Top. Med. Chem. 2009; 9: 58
• 3 Kameda Y, Asano N, Yoshikawa M, Matsui K. J. Antibiot. 1980; 33: 1573
• 4 Horii S, Iwasa T, Mizuta E, Kameda Y. J. Antibiot. 1971; 24: 59
• 5 Kameda Y, Asano N, Yoshikawa M, Takeuchi M, Yamaguchi T, Matsui K, Horii S, Fukase H. J. Antibiot. 1984; 37: 1301
• 6 Mahmud T. Nat. Prod. Rep. 2003; 20: 137
• 7a Pandey G, Tiwari KN, Puranik VG. Org. Lett. 2008; 10: 3611
• 7b Kurbanoglu NI, Celik M, Kilic H, Alp C, Sahin E, Balci M. Tetrahedron 2010; 66: 3485
• 7c Alegert C, Benet-Beholtz J, Riera A. Org. Lett. 2006; 8: 3069
• 7d Donohoe T, Johnson PD, Pye RJ, Keenan M. Org. Lett. 2005; 7: 1275
• 7e Gupta P, Pal AP. J, Reddy YS, Vankar YD. Eur. J. Org. Chem. 2011; 1166
• 7f Chakraborty C, Vyavahare VP, Puranik VG, Dhavale DD. Tetrahedron 2008; 64: 9574
• 7g Mehta G, Lakshminath S, Talukdar P. Tetrahedron Lett. 2002; 43: 335
• 7h Radha Krishna P, Reddy PS. Synlett 2009; 209

For some reports, see:
• 8a Gomez AM, Moreno E, Uriel C, Jarosz S, Valverde S, Lopez JC. Tetrahedron:Asymmetry 2005; 16: 2401
• 8b Diaz L, Casas J, Bujons J, Llebaria A, Delgado A. J. Med. Chem. 2011; 54: 2069
• 8c Diaz L, Bujons J, Casas J, Llebaria A, Delgado A. J. Med. Chem. 2010; 53: 5248
• 8d Ogawa S, Kobayashi Y, Kobayama K, Jimbo M, Inokuchi J. Bioorg. Med. Chem. 1998; 6: 1955

For some reports, see;
• 9a Mehta G, Mohanrao R, Katukojvala S, Landais Y, Sen S. Tetrahedron Lett. 2011; 52: 2893
• 9b Mehta G, Pallavi K, Katukojvala S. Tetrahedron Lett. 2009; 50: 4519
• 9c Shing TK. M, Wong WF, Ikeno T, Yamada T. Org. Lett. 2007; 9: 207
• 9d Girard E, Desvergnes V, Tarnus C, Landais Y. Org. Biomol. Chem. 2010; 8: 5628
• 9e Andriuzzi O, Gravier-Pelletier C, Bertho G, Prange T, le Merrer Y. Beilstein J. Org. Chem. 2005; 1: 12
• 9f Rassu G, Auzzas L, Pinna L, Zambrano V, Zanardi F, Battistini L, Gaetani E, Curti C, Casiraghi G. J. Org. Chem. 2003; 68: 5881

For some reports, see:
• 10a Kummeter M, Kazmaier U. Eur. J. Org. Chem. 2003; 3325
• 10b Jotterand N, Vogel P, Schenk K. Helv. Chim. Acta 1999; 82: 821
• 10c Kameda Y, Kawashima K, Takeuchi M, Ikeda K, Asano N, Matsui K. Carbohydr. Res. 1997; 300: 259
• 10d Ahmad S, Thomas LH, Sutherland A. Org. Biomol. Chem. 2011; 9: 2801
• 10e Sureshan KM, Ikeda K, Asano N, Watanabe Y. Tetrahedron 2008; 64: 4072
• 10f Podeschwa MA. L, Plettenburg O, Altenbach H. Org. Biomol. Chem. 2003; 1: 1919
• 10g Shing TK. M, Chen Y, Ng W. Tetrahedron 2011; 67: 6001
• 11a Garner P, Park JM. Org. Synth. 1991; 70: 18
• 11b Santoso S, Kemmer T, Trowitzsch W. Liebigs Ann. Chem. 1981; 658
• 11c Avenoza A, Cativiela C, Corzana F, Peregrina JM, Zurbano MM. Synthesis 1997; 1146
• 12 Chattopadhyay SK, Bandyopadhyay A. Tetrahedron Lett. 2011; 52: 3942
• 13a Garner P, Park JM. J. Org. Chem. 1983; 48: 4155
• 13b Herold P. Helv. Chim. Acta 1988; 71: 354
• 13c Bandyopadhyay A, Pal BK, Chattopadhyay SK. Tetrahedron: Asymmetry 2008; 19: 1875
• 14 Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
• 15 Cooke JW. B, Davies SG, Naylor A. Tetrahedron 1993; 49: 7955

For some reports on syn-selective addition to α-chiral α-aminoaldehydes, see:
• 16a Denis J.-N, Correa A, Greene AE. J. Org. Chem. 1991; 56: 6939
• 16b Ibuka T, Habashita H, Otaka A, Fujii N, Oguchi Y, Ueyhara T, Yamamoto Y. J. Org. Chem. 1991; 56: 4370
• 16c Ravikumar JS, Dutta A. Tetrahedron Lett. 1999; 40: 1381
• 16d Chattopadhyay SK, Roy SP. Tetrahedron Lett. 2008; 49: 5498
• 17 CCDC 896721 contains the crystal data for compound 22 [Unit cell parameters: a = 5.4911(8); b = 10.3246 (14); c = 13.684 (2); β = 101.172 (3). Space group: P21]. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: [phone], E-mail: [e-mail]].
• 18 For a recent report, see: Shih T.-L, Yang SY. Molecules 2012; 17: 4498

For some reviews on the topic, see:
• 19a Eckert H. Molecules 2012; 17: 1074
• 19b Arya P, Joseph R, Gan Z, Rakic B. Chem. Biol. 2005; 12: 163
• 19c Burke MD, Schreiber SL. Angew. Chem. Int. Ed. 2004; 43: 46
• 19d Spring DR. Org. Biomol. Chem. 2003; 1: 3867