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DOI: 10.1055/s-0029-1216926
New Applications of PhI(OAc)2 in Synthesis: Total Synthesis and SAR Development of Potent Antitumor Natural Product Psymberin/Irciniastatin A
Publikationsverlauf
Publikationsdatum:
07. August 2009 (online)
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Abstract
A novel PhI(OAc)2-mediated oxidative cyclization reaction is discovered for the synthesis of α-oxy N-acyl aminals and hemiaminals in good yields from readily synthesized N-acyl enamines. This methodology represents a cascade process to construct the core structure of the pederin family of natural products. The total synthesis of psymberin, a member of the pederin family, is accomplished using this ring-closure reaction as the key step. This new method is further showcased in the preparation of advanced psymberin analogues. The biological data of these analogues are presented.
1 Introduction
2 Methodology Development
3 Total Synthesis of Psymberin
4 Synthesis of Psymberin Analogues: The Discovery of C11-Deoxypsymberin
5 Conclusion
Key words
(diacetoxyiodo)benzene - psymberin - oxidative cyclization - total synthesis - antitumor
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