90687-23-3Relevant academic research and scientific papers
SHIKIMIC ACIDS FROM FURAN; METHODS OF STEREOCONTROLLED ACCESS TO 3,4,5-TRIOXIGENATED CYCLOHEXENES
Rajapaksa, D.,Keay, B. A.,Rodrigo, R.
, p. 826 - 828 (2007/10/02)
Oxabicycloheptenes 1 and 2 are converted to 3,4,5-oxigenated cyclohexenes by stereocontrolled hydroxylations and epoxidations coupled with reverse-Michael cleavage of the oxabicyclo system.Three epimers of shikimic acid are synthesized by these methods.
Anomalous 5-endo-trig reversals: general reactions of 7-oxabicycloheptenes and heptanes
Keay, B. A.,Rajapaksa, D,Rodrigo, R.
, p. 1093 - 1098 (2007/10/02)
Two general reversals of 7-oxabicycloheptanes are described and discussed.The reverse-Michael reaction occurs with the aldehyde, ketone, ester, and nitrile derivatives while the reverse aldol readtion catalysed by acid is confined to the aldehydes and ketones.The properties of the title compounds are rationalized in terms of the geometric alignments of the bonding and antibonding orbitals of the bridging oxygen atom and its neighboring carbons.New isobenzofuran and cyclohexadiene syntheses form a part of the report.
