Synthesis (and Alternative Proof of Configuration) of the Scyphostatin C(1‘)−C(20‘) Trienoyl Fragment
- 19 April 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (10), 1481-1483
- https://doi.org/10.1021/ol0058386
Abstract
Each of four diastereomers of structure 2, corresponding to the lipophilic side chain of scyphostatin (1), were prepared. Careful analysis of their NMR spectral data and comparison with those of the natural product corroborates the recently reported (Org. Lett. 2000, 2, 505) stereochemical assignment. A strategy for the stereoselective synthesis of 2 has been achieved.Keywords
This publication has 5 references indexed in Scilit:
- Synthesis of both top and bottom fragments of (-)-talaromycin A through enantiospecific and diastereoselective elaboration of asymmetrized tris (hydroxymethyl)methaneThe Journal of Organic Chemistry, 1993
- Synthesis and transannular Diels–Alder reaction of a 13-membered macrocyclic triene having a tetrasubstituted enol ether as dienophileCanadian Journal of Chemistry, 1990
- A High Resolution 23Na NMR Study of Sodium Complexes with Ionophores in Solution. Stability of Complexes as Viewed from Displacements of 23Na Chemical Shifts as Referred to Those in the Solid StateBulletin of the Chemical Society of Japan, 1987
- Practical asymmetric synthesis of aklavinoneJournal of the American Chemical Society, 1982
- Effect of Structure on Reactivity. XI. Hydrazinolysis of Ethyl AcetateJournal of the American Chemical Society, 1957