112563-46-9Relevant academic research and scientific papers
Olivanic Acid Analogues. Part 9. Allylic Oxidative Functionalisation of Substituted Azetidinones: Synthesis of Some 4-Acyloxy-7-oxo-1-azabicyclohept-2-ene-2-carboxylates
Bateson, John H.,Robins, Alison M.,Southgate, Robert
, p. 2399 - 2405 (2007/10/02)
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-azabicyclooct-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.
SYNTHESIS OF SOME 4-ACYLOXY-7-OXO-1-AZABICYCLOHEPT-2-ENE-2-CARBOXYLATES
Bateson, John H.,Quinn, Alison M.,Southgate, Robert
, p. 1561 - 1564 (2007/10/02)
Allylic oxidation of 4-allyl-1-dimethyl-t-butylsilylazetidin-2-ones (5,7) gave the 4-(1-hydroxyprop-2-ene-1-yl) derivatives (6,8).Radical benzoyloxylation of the silylated 8-oxo-7-azabicyclooct-3-ene (18) provided four allylic monobenzoates.Progression of (8) and (29) afforded, respectively, 4-acyloxy olivanic acid analogues containing trans- (16) and cis- (31) substituents at C-6.
