Total Synthesis of Passifetilactone D, Cryptorigidifoliol I, and Cryptorigidifoliol B Isomers Enabled by Ghosez
Sagar B Khandekar1, Rodney A Fernandes1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, Maharashtra, India.
Abstract:
A concise and efficient asymmetric total synthesis of bicyclic-THP-lactone natural products passifetilactone D and cryptorigidifoliol I and four of the stereoisomers of proposed cryptorigidifoliol B has been achieved, enabled by Maruoka/Reetz or Maruoka/Brown allylations and Ghosez lactonization. Although the required diastereomers of cryptorigidifoliol B are synthesized now, with the mismatch of data to that of the natural isolate, its actual structure could not be ascertained, indicating a need for further structure revision.
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