Configuration of the Psymberin Amide Side Chain
- 15 June 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (14) , 2905-2908
- https://doi.org/10.1021/ol0508375
Abstract
[structure: see text] The structure of the amide side chain of psymberin, a potent and selective cytotoxin, is proposed. Syn and anti models of the amide side chain were prepared, and the structural assignment was confirmed by X-ray crystallographic analysis of the anti isomer. Comparison of (1)H and (13)C NMR data establishes homology between the natural product and the synthetic model compound of anti configuration and not the corresponding syn isomer.Keywords
This publication has 12 references indexed in Scilit:
- Psymberin, A Potent Sponge-Derived Cytotoxin from Psammocinia Distantly Related to the Pederin FamilyOrganic Letters, 2004
- Universal NMR Databases for Contiguous PolyolsJournal of the American Chemical Society, 2003
- Tuning the Regiospecificity of Cleavage in FeIII Catecholate Complexes: Tridentate Facial versus Meridional LigandsPublished by Wiley ,2000
- Stereochemical Determination of Acyclic Structures Based on Carbon−Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural ProductsThe Journal of Organic Chemistry, 1999
- Absolute Configuration of Phorboxazoles A and B from the Marine Sponge Phorbas sp. 1. Macrolide and Hemiketal RingsJournal of the American Chemical Society, 1996
- A One Pot Procedure for the Synthesis of ?-Hydroxyamides from the Corresponding ?-HydroxyacidsSynthetic Communications, 1992
- Synthesis of 2,3-O-isopropylidene-D-glyceraldehyde in high chemical and optical purity: observations on the development of a practical bulk processThe Journal of Organic Chemistry, 1991
- Halogenated epoxides. 9. Reaction of trans-2,3-dichlorooxirane with dimethyl sulfideThe Journal of Organic Chemistry, 1986
- Organic reactions of sulfur dioxide. Reactions with nucleophilic double bonds leading to the isomerization, aromatization, selective hydrogen-deuterium exchange, and electron-transfer processesThe Journal of Organic Chemistry, 1983
- On the steric course of the addition of some organometallic reagents to (R)-2,3-isopropylidene glyceraldehyde. Synthesis of optically active α-benzyloxy aldehydes, alcohols, carboxylic acids and 1,2-diols.Tetrahedron Letters, 1983