A general approach to indolizidine alkaloids from 1-benzyloxy-5-(p-toluenesulfonamido)-3-alken-2-ols: synthesis of (+)-monomorine I

Abstract

A versatile method for the preparation of indolizidine alkaloids from 1-benzyloxy-5-(p-toluenesulfonamido)-3-alken-2-ols as stereodefined key intermediates has been developed. The utility of this approach was demonstrated by the synthesis of (+)-monomorine I.PT: J; CR: BACKVALL JE, 1990, J ORG CHEM, V55, P826 BAILEY AJ, 1993, INORG CHEM, V32, P268 BERRY MB, 1997, CHEM COMMUN 1121, P2141 CUNY GD, 1995, SYNLETT, P519 DALY JW, 1983, SCIENCE, P705 DALY JW, 1986, ALKALOIDS CHEM BIOL, V4, CH1 GAO Y, 1995, J AM CHEM SOC, V117, P5399 GRIFFITH WP, 1987, J CHEM SOC CHEM COMM, P1625 GRIFFITH WP, 1990, ALDRICHIM ACTA, V23, P13 HAMADA Y, 1987, J ORG CHEM, V52, P1252 HOWARD AS, 1986, ALKALOIDS, V28, CH6 ITO M, 1991, TETRAHEDRON, V47, P9329 KROHN K, 1998, J PRAK CHEM-CHEM ZTG, V340, P26 MICHAEL JP, 1995, NAT PROD REP, V12, P535 MOMOSE T, 1997, J CHEM SOC PERK 0507, P1315 MUNCHHOF MJ, 1995, J AM CHEM SOC, V117, P5399 NUMATA A, 1987, ALKALOIDS, V31, CH3 PARIKH JR, 1967, J AM CHEM SOC, V89, P5505 PETTERSSONFASTH H, 1995, J ORG CHEM, V60, P6091 PETTERSSONFASTH P, 1994, THESIS UPPSALA U RITTER FJ, 1973, EXPERIENTIA, V29, P530 ROYER J, 1985, J ORG CHEM, V50, P670 SALIOU C, 1991, TETRAHEDRON LETT, V32, P3365 SHAWE TT, 1994, J ORG CHEM, V59, P5841 SOMFAI P, 1997, ACTA CHEM SCAND, V51, P1024 STEVENS RV, 1982, J CHEM SOC CHEM COMM, P102 STOWELL JC, 1979, SYNTHESIS-STUTTGART, P132 STOWELL JC, 1990, ORG SYNTH COLL, V7, P140 TAKAHATA H, 1993, ALKALOIDS, V44, CH3 TAKAHATA H, 1993, HETEROCYCLES, V36, P2777 TOKUYAMA T, 1986, TETRAHEDRON, V42, P3453 TROST BM, 1978, J AM CHEM SOC, V100, P3426 YAMAGUCHI R, 1987, J ORG CHEM, V52, P2094 YAMAZAKI N, 1988, TETRAHEDRON LETT, V29, P5767 YAMAZAKI N, 1989, J AM CHEM SOC, V111, P1396; NR: 35; TC: 9; J9: EUR J ORG CHEM; PG: 4; GA: 313PNSource type: Electronic(1