111649-71-9Relevant articles and documents
Rhodium-catalyzed endo -selective epoxide-opening cascades: formal synthesis of (-)-brevisin
Armbrust, Kurt W.,Beaver, Matthew G.,Jamison, Timothy F.
, p. 6941 - 6946 (2015/06/16)
[Rh(CO)2Cl]2 is as an effective catalyst for endo-selective cyclizations and cascades of epoxy-(E)-enoate alcohols, thus enabling the synthesis of oxepanes and oxepane-containing polyethers from di- and trisubstituted epoxides. Synth
Studies Directed toward the Total Synthesis of Azaspiracid: Stereoselective Construction of C1-C12, C13-C19, and C21-C25 Fragments
Carter, Rich G.,Weldon, David J.
, p. 3913 - 3916 (2007/10/03)
equation presented The efficient entry to the C1-C12, C13-C19, and C21-C25 fragments of azaspiracid is outlined. The C1-C12 portion is constructed using a key asymmetric allenyl borane addition to the corresponding α,β-unsaturated aldehyde. The synthesis of the C13-C19 portion utilizes an Evans asymmetric alkylation followed by Sharpless asymmetric dihydroxylation. In addition, a novel solution to the mismatched effects of a neighboring chiral oxazolidinone during a Sharpless dihydroxylation is detailed.
Tandem radical cyclizations on lodoaryl azides: synthesis of the core tetracycle of aspidosperma alkaloids
Kizil, Murat,Patro, Balaram,Callaghan, Owen,Murphy, John A.,Hursthouse, Michael B.,Hibbs, Dai
, p. 7856 - 7862 (2007/10/03)
A new stereoselective approach to the tetracyclic core of Aspidosperma alkaloids is described. Selective attack by tristrimethylsilylsilyl radicals on the aryl carbon-iodine bond of iodoaryl azides was first demonstrated on the simple model 15, thus both extending the recent discoveries of Kim and co-workers on aliphatic C-I bonds and demonstrating that the selectivity can be exploited in cascade radical cyclizations. Extension to the more complex substrate 25 afforded the core ABCE tetracyclic skeleton of the alkaloids in excellent yield and with efficient control of relative stereochemistry.
