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Degradation and partial reconstruction (C3-C14) of cytotoxic macrolide palmerolide A
As part of our program to investigate the chemical diversity of cold-water marine organisms , we recently reported the structure of palmerolide A , an enamide-bearing macrolide isolated from the Antarctic tunicate Synoicum adareanum. The structure of palmerolide A was elucidated using a combination of spectroscopic and derivatization techniques . We have subjected palmerolide A to degradative studies to confirm the stereochemical assignments which has resulted in re-assignment of the C7, 10 and 11 stereocenters . Analogs of the expected degradation products were prepared via a chiral pool synthetic approach. With the correct absolute configuration at C7, 10, and 11 determined, our efforts were directed toward the reconstruction of palmerolide A using similar synthetic routes devised to generate the chiral polyols in our degradation study. Partial synthesis (C3-C14) of palmerolide A was achieved by means of the above mentioned chiral-pool approach.
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