195873-65-5Relevant academic research and scientific papers
Straightforward synthesis of diverse 1-deoxyazapyranosides via stereocontrolled nucleophilic additions to six-membered cyclic nitrones
Chan, Ting-Hao,Chang, Yi-Fan,Hsu, Jung-Jung,Cheng, Wei-Chieh
supporting information; experimental part, p. 5555 - 5559 (2011/01/05)
A systematic study of diastereoselective nucleophilic addition of Grignard reagents to six-membered chiral tri-O-benzyl cyclic nitrones is described. With all eight chiral cyclic nitrones and asymmetric reaction conditions in hand, a practical methodology is established for the preparation of diverse 1-deoxyazapyranosides bearing various stereogenic centers. We have developed practical methods to prepare all eight six-membered chiral cyclic nitrones. Using these cyclic nitrones and diastereoselective nucleophilic additions, 12 examples of diverse 1-deoxyazapyranosides including enantiomers were synthesized to demonstrate the generality and flexibility of this new approach.
Synthesis and biological evaluation of aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F structurally related to the amaryllidaceae anticancer constituents
Kireev, Artem S.,Nadein, Oleg N.,Agustin, Vincent J.,Bush, Nancy E.,Evidente, Antonio,Manpadi, Madhuri,Ogasawara, Marcia A.,Rastogi, Shiva K.,Rogelj, Snezna,Shors, Scott T.,Kornienko, Alexander
, p. 5694 - 5707 (2007/10/03)
Pancratistatin is a potent anticancer natural product, whose clinical evaluation is hampered by the limited natural abundance and the stereochemically complex structure undermining practical chemical preparation. Fifteen aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F that possess four of the six pancratistatin stereocenters have been synthesized and evaluated for anticancer activity. These compounds serve as truncated pancratistatin analogues lacking the lactam ring B, but retaining the crucial C10a-C10b bond with the correct stereochemistry. The lack of activity of these compounds provides further insight into pancratistatin's minimum structural requirements for cytotoxicity, particularly the criticality of the intact phenanthridone skeleton. Significantly, these series provide rare examples of simple aromatic conduritol and inositol analogues and, therefore, this study expands the chemistry and biology of these important classes of compounds.
An approach to pancratistatins via ring-closing metathesis: Efficient synthesis of novel 1-aryl-1-deoxyconduritols F
Nadein, Oleg N.,Kornienko, Alexander
, p. 831 - 834 (2007/10/03)
Structurally novel cyclitols, 1-aryl-1-deoxyconduritols F, were efficiently prepared from D-xylose, utilizing RCM as a key step. Various aromatic residues were incorporated in the cyclitol skeleton with total stereochemical control, utilizing a diastereoselective aryl cuprate addition to a γ-alkoxy enoate. The synthetic route establishes a firm foundation for a practical synthesis of the antitumor alkaloid pancratistatin and its aryl analogues.
Synthesis of cyclitols via ring-closing metathesis
Kornienko, Alexander,D'Alarcao, Marc
, p. 827 - 829 (2007/10/03)
A convenient synthesis of enantiomerically pure and differentially protected L-chiro- and myo-inositols as well as conduritols B and F from 2,3,4-tri-O-benzyl-D-xylopyranose via ring-closing metathesis is reported. The facile synthesis of conduritol B con
Enantiospecific synthesis of a differentially protected L-chiro-inositol from D-xylose
Kornienko, Alexander,D'Alarcao, Marc
, p. 6497 - 6500 (2007/10/03)
A convenient synthesis of differentially protected L-chiro-inositol 7 from 2,3,4-tri-O-benzyl-D-xylopyranose is described The structure of 7 was confirmed by its transformation to the pentabenzylated derivative of(-)quebrachitol.
