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The Total Synthesis of (−)‐Callystatin A

2003; Wiley; Volume: 9; Issue: 5 Linguagem: Inglês

10.1002/chem.200390130

1521-3765

Markus Kalesse, K. Purushothama Chary, Monika Quitschalle, Arne Burzlaff, Cornelia Kasper, Thomas Scheper,

Oxidative Organic Chemistry Reactions

Abstract Callystatin A is a prominent member of a class of natural products which display promising growth inhibition of cancer cells in their biological profile. The challenging structure and the interesting biological activity of (−)‐callystatin A fueled our interest in the synthesis of this marine natural product. We achieved the total synthesis using a highly convergent approach joining four subunits together with a Wittig olefination, a selective Heck reaction and an aldol reaction as the pivotal steps. The aldol reaction as one of the final transformations during the synthesis opens fast access to a variety of structural analogues and circumvents tedious protecting group manipulations. Here we report an improved synthesis utilizing a modified vinyl iodide which shortens the synthesis by two steps. Additionally, first biological results will be reported.