Organic Letters
Organic Letters
5 years ago

Total Synthesis of (−)-Phorbaketal A

Total Synthesis of (−)-Phorbaketal A
Hee-Yoon Lee, Rira Kim, Seewon Joung
A convergent asymmetric total synthesis of phorbaketal A was achieved in 10 steps through a Au(I)-catalyzed intramolecular spiroketalization reaction of an alkyne diol intermediate prepared from (R)-carvone and geranial. The spiroketalization reaction was regio- and stereoselective and was accompanied by isomerization of an exo-olefin into the trisubstituted olefin to form a unique spiroketal structure of phorbaketals.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01797

DOI: 10.1021/acs.orglett.7b01797

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