Enantioselective Total Synthesis of Batzelladine A

摘要

Batzelladines A-I are members of a class of polycyclic guanidine alkaloids that were isolated from Bahamian and Jamaican sponges by scientists at SmithKline Beecham in 1995 and 1997. The batzelladines are of much interest, as batzelladines A (1), B, and D (2) inhibit the binding of the HIV glycoprotein gpl20 to the human CD4 receptor, whereas batzelladines F-I were found to dissociate the protein tyrosine kinase p56lck from CD4. The unique structures of the batzelladines and their potential clinical importance in AIDS treatment have inspired considerable synthetic attention. In 1998, Snider and Chen reported the total synthesis of batzelladine E (3) by a biomimetic synthetic route; this was the first synthetic success in this class of molecules.