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Total Synthesis of Beshanzuenone D and Its Epimers and Abiespiroside A by Balasaheb R. Borade; Ruchi Dixit; Ravindar Kontham is a Chemistry article available to read on EtoBox.

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A unified and protecting-group-free six-step total synthesis of bisabolane-type sesquiterpenoid beshanzuenone D and its stereoisomers and abiespiroside A using -(+)-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 O) 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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Author

Balasaheb R. Borade; Ruchi Dixit; Ravindar Kontham

Publisher

American Chemical Society; American Chemical Society (ACS); Test accounts (ISSN 1523-7060)

Published

2020

Language

EN

Field

Chemistry (Physical Sciences)