THE PLANT ALKALOIDS

By MATTHEW DAVIS

CONTENTS LYCOPODIUM ALKALOIDS: ISOLATION AND ASYMMETRIC SYNTHESIS SYNTHESIS OF MORPHINE ALKALOIDS AND DERIVATIVES INDOLE PRENYLATION IN ALKALOID SYNTHESIS MARINE PYRROLOIMINOQUINONE ALKALOIDS SYNTHETIC STUDIES ON AMARYLLIDACEAE AND OTHER TERRESTRIALLY DERIVED ALKALOIDS SYNTHESIS OF PYRROLE AND CARBAZOLE ALKALOIDS LYCOPODIUM ALKALOIDS: ISOLATION AND ASYMMETRIC SYNTHESIS ABSTRACT LYCOPODIUM ALKALOIDS HAVE ATTRACTED THE ATTENTION OF MANY NATURAL PRODUCT CHEMISTS AND SYNTHETIC ORGANIC CHEMISTS DUE TO THEIR IMPORTANT BIOLOGICAL ACTIVITIES AND UNIQUE SKELETAL CHARACTERISTICS IN THIS REVIEW WE DESCRIBE ISOLATION AND ASYMMETRIC SYNTHESES OF SEVERAL NEW ALKALOIDS SUCH AS LYCOPOSERRAMINES-C, -V, -W, AND CERNUINE, AND SHOW THAT ASYMMETRIC TOTAL SYNTHESIS PLAYED A KEY ROLE IN ELUCIDATING THE STRUCTURES OF THESE COMPLEX NATURAL PRODUCTS KEYWORDS ALKALOID ASYMMETRIC SYNTHESIS ISOLATION LYCOPODIUM STRUCTURE ELUCIDATION INTRODUCTION FAWCETTIMINE-TYPE ALKALOIDS LYCOPOSERRAMINE-A LYCOPOSERRAMINE-B LYCOPOSERRAMINE-C PHLEGMARINE-TYPE ALKALOIDS LYCOPOSERRAMINE-V LYCOPOSERRAMINE-W LYCOPOSERRAMINES-X AND -Z CERNUINE AND RELATED ALKALOIDS ESTABLISHMENT OF AN EF?CIENT ROUTE TO A COMMON SYNTHETIC INTERMEDIATE QUINOLIZIDINE-TYPE ALKALOIDS CERNUANE-TYPE ALKALOIDS CONCLUSION REFERENCES