3883-56-5Relevant articles and documents
Structural studies of the mycotoxin verrucosidin
Ganguli,Burka,Harris
, p. 3762 - 3766 (1984)
-
Thermal Isomerization of Isodicyclopentadiene and Its Cycloaddition Reactions
Subramanyam, Ravi,Batlett, Paul D.,Iglesias, Graciela Y. Moltrasio,Watson, William H.,Galloy, Jean
, p. 4491 - 4498 (1982)
Isodicyclopentadiene (4) undergoes a sigmatropic hydrogen shift at elevated temperatures (170-180 deg C) to form an isomeric, higly reactive diene intermediate 5 which readily undergoes cycloaddition reactions with dienophiles like dichlorovinylene carbonate (DCVC, 8), vinylene carbonate (VC, 7), and maleic anhydride (9).In all cases addition to 5 occurs exclusively from the exo face.While 7 and 8 under these high-temperature conditions give one major addition product each (12 and 13, respectively), in accord with Alder's rule, 9 at high temperature yields the two isomeric product 15 and 16 initially in the ratio 1:3 of which the isomer 16 (Alder's rule product) on prolonged heating is converted into the stable isomer 15 (anti Alder's rule product).The cycloaddition reactions of 4-cyclopentene-1,3-dione (10), 2,2-dimethyl-4-cyclopentene-1,3-dione (11), and dimethyl acetylenedicarboxylate (28) with 4 and 5 are also discussed.In situ formation of 5 at 0 deg C by photolytic cleavage of diketone 14 is proved by trapping 5 with maleic anhydride.X-ray crystallographic data are provided for the adducts 12, 13, 15, 16, and 21.
Structures of cyclopentanepolyones.
Hiraga
, p. 1300 - 1306 (1965)
-
Synthetic studies toward sordarin: Building blocks for the terpenoid core and for analogues thereof
Schule, Arnaud,Liang, Huan,Vors, Jean-Pierre,Ciufolini, Marco A.
supporting information; experimental part, p. 1587 - 1597 (2009/07/24)
Avenues to bi- and tricyclic building blocks for the elaboration of sordaricin and its analogues are described. The target molecules were obtained through inter- and intramolecular Diels-Alder reactions of a number of previously unknown cyclopentadienes. Unusual properties of 3-cyanoenones and 1-cyanocyclopen-tadienes have been unveiled and circumvented.
Moenomycin A: New chemistry that allows to attach the antibiotic to reporter groups, solid supports, and proteins
Kempin, Uwe,Hennig, Lothar,Knoll, Dietmar,Welzel, Peter,Mueller, Dietrich,Markus, Astrid,Van Heijenoort, Jean
, p. 17669 - 17690 (2007/10/03)
Moenomycin A (18) on reaction with the diazonium salt derived from bifunctional (protected) 15 yields the coupling product 19 which on reduction is converted into the moenomycin thiol derivative 21. Thiol 21 has been used to prepare selectively moenomycin dansyl and biotin adducts 26 and 28, respectively. This work was performed with the aim to use moenomycin as a tool for studies of the transglycosylation step in peptidoglycan biosynthesis.