35827-71-5Relevant academic research and scientific papers
THE TOTAL SYNTHESES OF (-)-INDICINE N-OXIDE AND INTERMEDINE N-OXIDE
Nishimura, Yoshio,Kondo, Shinichi,Umezawa, Hamao
, p. 4323 - 4326 (2007/10/02)
The total syntheses of (-)-indicine N-oxide, the enantiomer of natural indicine N-oxide and intermedine N-oxide have been achieved.
The Photochemistry of Ketones Derived from Carbohydrates. Part 10. A Study of Stereochemical Influences on Photo-induced Rearrangements and Ring Expansions of 3-Oxacyclopentanones Using 1,2-O-Isopropylidenefuranos-3-ulose Derivatives
Collins, Peter M.,Farnia, Farnoosh
, p. 575 - 582 (2007/10/02)
U.v.-irradiation of the 3-oxacyclopentanone 5-deoxy-1,2-O-isopropylidene-β-D-threo-pentofuranos-3-ulose (9) in methanol gave at -60 deg C, and to a small extent at +20 deg C, -2,3-isopropylidenedioxy-5-methoxy-6-methyl-1,4-dioxane (12), whereas in a benzene solution at +20 deg C only the unsaturated lactones 2,2-dimethyl-5--1,3-dioxolan-4-one (13) and its (E)-isomer (14) were obtained.The photoproducts formed from (9) in methanol-diethyl ether (1:4) at -60 deg C were a mixture of the dioxane (12) and the lactones (13) and (14).The isomeric erythro-ulose (20) gave only the lactones (13) and (14) when irradiated in either methanol-diethyl ether (1:4) at -60 deg C or in benzene at +20 deg C.The lactone mixtures from (9) and (20) possessed similar specific optical rotations.U.V.-irradiation of a benzene solution of 1,2-O-isopropylidene-α-L-glycero-tetrofuranos-3-ulose (22) at +20 deg C gave racemic 5-ethenyloxy-2,2-dimethyl-1,3-dioxolan-4-one (16).The optical activity exhibited by the lactone mixtures produced from ketones (9), (20) and (22) indicated that they were not formed via the respective oxacarbenes (11), (29) and (30), which are chiral, but through the intermediacy of the symmetric enals (31) from (9) and (20), and (32) from (22).The uloses (9) and (20) formed hemiacetals (18), and (23) and (24) respectively, in methanolic solutions but only to a limited extent at low temperatures.
