A Facile Asymmetric Synthesis of Tetrahydroisoquinoline and Tryptoline Derivatives with a Quaternary Carbon Center at C(3)

Abstract

Optically active tetrahydroisoquinoline and tryptoline derivatives with a quaternary carbon center at C(3) were prepared from l-DOPA and l-tryptophan, respectively.

Key words

heterocycles - asymmetric synthesis - amino acids - axial chirality - Pictet-Spengler reaction

References

• 1 Scott JD. Williams RM. Chem. Rev.  2002,  102:  1669 
• 2 Yamakawa T. Ohta S. Biochem. Biophys. Res. Commun.  1997,  236:  676 
• 3 Gibson SE. Gullio N. Tozer MJ. Tetrahedron  1999,  55:  585 
• 4 Salvadoli S. Balboni G. Guerrini R. Tomatis R. Bianchi C. Bryant SD. Cooper PS. Lazarus LH. J. Med. Chem.  1997,  40:  3100 
• For recent examples see:
• 5a Spengler J. Schedel H. Sieler J. Quaedflieg PJLM. Broxterman QB. Duchateau ALL. Barger K. Synthesis  2001,  1513 
• 5b Meziane MAA. Royer S. Bazureau JP. Tetrahedron Lett.  2001,  42:  1017 
• 5c Davis FA. Mohanty PK. Burns DM. Andemichael YW. Yemane W. Org. Lett.  2000,  2:  3901 
• 5d Jullian V. Quirion J.-C. Husson H.-P. Eur. J. Org. Chem.  2000,  1319 
• 5e Taniyama D. Hasegawa M. Tomioka K. Tetrahedron: Asymmetry  1999,  10:  221 
• 5f Huber IMP. Seebach D. Helv. Chim. Acta  1987,  70:  1944 
• For recent examples of excellent methods for preparation of quaternary tetrahydroisoquinoline-3-carboxylic acid derivatives see:
• 6a Alezra V. Bonin M. Micouin L. Husson H.-P. Tetrahedron Lett.  2001,  42:  2111 
• 6b Ooi T. Takeuti M. Moruoka K. Synthesis  2001,  1716 
• 7 Kawabata T. Suzuki H. Nagae Y. Fuji K. Angew. Chem. Int. Ed.  2000,  39:  2155 
• 8a Kawabata T. Yahiro K. Fuji K. J. Am. Chem. Soc.  1991,  113:  9694 
• 8b Kawabata T. Wirth T. Yahiro K. Suzuki H. Fuji K. J. Am. Chem. Soc.  1994,  116:  10809 
• 8c Fuji K. Kawabata T. Chem.-Eur. J.  1998,  4:  373 
• 8d Kawabata T. Chen J. Suzuki H. Nagae Y. Kinoshita T. Chancharunee S. Fuji K. Org. Lett.  2000,  2:  3883 
• 8e Kawabata T. Kawakami S. Fuji K. Tetrahedron Lett.  2002,  43:  1465 
• 9 Acid-catalyzed cyclization of α-methoxyalkylcarbamates has been reported as an alternative to Pictet-Spengler recation see: Cheung GK. Earle MJ. Fairhurst RA. Heaney H. Shuhaibar KF. Eyley SC. Ince F. Synlett  1991,  721 
• 10 Depew KM. Marsden SP. Zatorska D. Zatorski A. Bornamnn WG. Danishefsky SJ. J. Am. Chem. Soc.  1999,  121:  11953 
• 11 Brown CA. J. Org. Chem.  1974,  39:  3913