82416-07-7Relevant academic research and scientific papers
Conformationally constrained ACPD analogues. Synthesis and resolution of 3-aminobicyclo[3,3,0]octane-1,3-dicarboxylic acids
Ezquerra,Ezquerra, Jesus,Yruretagoyena,Yruretagoyena, Belen,Avendano,Avendano, Carmen,De La Cuesta,De La Cuesta, Elena,Gonzalez,Gonzalez, Rosario,Prieto,Prieto, Lourdes,Pedregal,Pedregal, Carmen,Espada,Espada, Modesta,Prowse,Prowse, William
, p. 3271 - 3278 (1995)
The synthetic of racemic 3-aminobicyclo[3.3.0]octane-1,3-dicarboxylic acids (2 and 3) which are conformationally constrained ACPD analogues, has been achieved in seven steps starting from the readily available Weiss diketone (4). Partial reduction of 4 to
REACTION OF DIMETHYL SODIO-3-KETOGLUTARATE WITH GLYOXAL AND SUBSTITUTED GLYOXALS; FIRST EXPEDITIOUS PREPARATION OF BICYCLOOCTANE-3,7-DIONE; SYNTHESIS AND CRYSTAL STRUCTURE OF 5,7-DIHYDROXY-4-METHOXYCARBONYL-3-PHENYL-1-INDANONE
Bertz, Steven H.,Rihs, G.,Woodward, R.B.
, p. 63 - 70 (2007/10/02)
A simple and efficient two-step preparation of bicyclooctane-3,7-dione starting from the sodium enolate of dimethyl 3-ketoglutarate and glyoxal is described.This is an unprecedented case in which a condensation reaction of glyoxal is more successful under vigorous conditions (refluxing methanol) than under much milder ones (buffered water at ambient temperature).The major product (after hydrolysis-decarboxylation) from the analogous sequence with phenylglyoxal is 5,7-dihydroxy-4-methoxycarbonyl-3-phenyl-1-indanone, the result of a Dieckmann reaction in addition to the Michael and aldol reactions.Only the latter two occur in aqueous buffers, where the product after hydrolysis-decarboxylation is 1-phenylbicyclooctane-3,7-dione.The X-ray crystal structure of the indanone reveals a novel hydrogen bonding phenomenon.
