Synthetic studies on spiroketal natural products. V. Total synthesis of (+)-talaromycin A and (-)-talaromycin B

Article abstract of DOI:10.1248/cpb.41.946

The total synthesis of (+)-talaromycin A and (-)-talaromycin B was accomplished by utilizing a common intermediate (3). The spiroketal (3) was converted to the olefin (4) via thermolysis of the sulfinyl group, C1-unit elongation at the C9-position, and isomerization at the spiro center. On the other hand, 3 was isomerized to 7 at the C9-position and then converted to the olefin (5) in a similar manner to that described for (+)-talaromycin A. These intermediates (4 and 5) were transformed into (+)-talaromycin A and (-)-talaromycin B via addition reaction of trifluoroacetic acid and oxymercuration, respectively.

Full text of DOI:10.1248/cpb.41.946

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