103084-92-0Relevant articles and documents
Novel reactions of indium reagents with 1,2-diones: A facile synthesis of α-hydroxy ketones
Nair, Vijay,Jayan,Ros, Sindu
, p. 9453 - 9459 (2001)
Indium mediated reactions of allyl, cinnamyl, propargyl and benzyl bromides, ethyl bromoacetate and ethyl-4-bromocrotonate with 1,2-diones, in the presence of sodium iodide, occur efficiently to afford α-hydroxy keto compounds in excellent yields.
Total synthesis and stereochemical assignment of (-)-ushikulide A
Trost, Barry M.,O'Boyle, Brendan M.,Hund, Daniel
supporting information; experimental part, p. 15061 - 15074 (2010/01/30)
We report the determination of the full stereostructure of (-)-ushikulide A (1), a spiroketal containing macrolide by total synthesis. Ushikulide A (1) was isolated from a culture broth of Streptomyces sp. IUK-102 and exhibits potent immunosuppressant activity (IC50 = 70 nM). To embark upon an ushikulide A synthesis, a tentative assignment was made based on analogy to cytovaricin (2), a related macrolide isolated from a culture of Streptomyces diastatochromogenes whose full structure was previously established via synthesis and X-ray crystallography. This report delineates studies on several key steps, namely a direct aldol reaction catalyzed by the dinuclear zinc ProPhenol complex, a metal catalyzed spiroketalization, as well as application of an unprecedented asymmetric alkynylation of a simple saturated aldehyde with methyl propiolate to prepare the nucleophilic partner for a Marshall-Tamaru propargylation. These studies culminated in the first total synthesis and stereochemical assignment of (-)-ushikulide A and significantly extended the scope of the above-mentioned methodologies.
Indium mediated Barbier reactions of 1,2-diones: A facile synthesis of α-hydroxy ketones
Nair, Vijay,Jayan
, p. 1091 - 1094 (2007/10/03)
Indium mediated allylation and cinnamylation of 1,2-diones with the corresponding bromides in the presence of sodium iodide produce α-carbonyl homoallylic alcohols in excellent yields. (C) 2000 Elsevier Science Ltd.