Journal of the Chemical Society. Perkin transactions I p. 2399 - 2405 (1991)
Update date:2022-08-06
Topics:
Bateson, John H.
Robins, Alison M.
Southgate, Robert
Sharpless oxidation (ButO2H), SeO2) of the protected allyl azetidinone 7 gave the allylic alcohol 8 which was transformed to the 5,6-trans-4α-acetoxyolivanic acid derivative 16.Kharasch-Sosnovsky benzoyloxylation (PhCO3But, CuCl, PhH, heat) of the silylated 7-azabicyclo<4.2.0>oct-3-enes 17b,c provided inter alia allylic benzoates 18b,c and 21b,c.These were synthetic precursors of the 5,6-cis-olivanic acid analogues 23 and 26, which contain 8- and 4α-benzoyloxy groups, respectively.
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