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Published on: June 13, 2022
Total Synthesis of Beshanzuenone D and Its Epimers and Abiespiroside A
Balasaheb R Borade1, Ruchi Dixit1, Ravindar Kontham1
1Academy of Scientific and Innovative Research (AcSIR), Ghaziabad-201002, India.
Abstract:
A unified and protecting-group-free six-step total synthesis of bisabolane-type sesquiterpenoid beshanzuenone D and its stereoisomers and abiespiroside A using S-(+)-carvone as a common chiral-pool building block is disclosed. This synthetic route features chemoselective allylic chlorination of carvone, Au(I)-catalyzed cycloisomerization induced construction of furan from homopropargylic diol, substrate-controlled selective hydroxylation using Davis-oxaziridine, and dye-sensitized photo-oxidation (through 1O2) of hydroxyalkyl tethered furan to access oxaspirolactone as key transformations. A comprehensive set of NMR data along with DFT calculations, ECD spectra, and optical rotation measurements of the synthesized beshanzuenone D and its epimers were obtained to confirm absolute configurations.
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