The structural and synthetic implications of the biosynthesis of the calycanthaceous alkaloids, the communesins, and nomofungin

A comparison is made between the calycanthaceous alkaloids, nomofungin, and the communesins using structural and biosynthetic information from studies of the former to shed light on the structural ambiguity of the two latter species. Also, a novel biosynthetic approach for the communesins is presented that involves coupling of tryptamine with the ergot alkaloid aurantioclavine that is suitable for synthetic emulation. Preliminary synthetic studies and inter-mediates are reported. (c) 2006 Elsevier Ltd. All rights reserved.