Synthetic Studies on Spiroketal Natural Products. V. Total Synthesis of (+)-Talaromycin A and (-)-Talaromycin B.
1993; Pharmaceutical Society of Japan; Volume: 41; Issue: 5 Linguagem: Inglês
10.1248/cpb.41.946
ISSN1347-5223
AutoresC. IWATA, Naoyoshi Maezaki, Kohji Hattori, Masahiro Fujita, Yasunori Moritani, Yoshiji Takemoto, Tetsuaki Tanaka, Takeshi Imanishi,
Tópico(s)Synthesis and Biological Activity
ResumoThe 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.
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