Studies Toward the Synthesis of (−)-Zampanolide: Preparation of N-Acyl Hemiaminal Model Systems

作者: Dawn M. Troast , John A. Porco

DOI: 10.1021/OL025558L

关键词:

摘要: Synthesis of N-acyl hemiaminal model systems related to the side chain antitumor natural product zampanolide is reported. Key steps involve oxidative decarboxylation N-acyl-α-amino acid intermediates, followed by ytterbium triflate mediated solvolysis. Evidence for stabilization moiety in compounds an intramolecular hydrogen-bonding network described.

参考文章(19)
Eugene P. Boden, Gary E. Keck, Proton-transfer steps in Steglich esterification: a very practical new method for macrolactonization Journal of Organic Chemistry. ,vol. 50, pp. 2394- 2395 ,(1985) , 10.1021/JO00213A044
David Askin, Christof Angst, Samuel Danishefsky, An approach to the synthesis of bactobolin and the total synthesis of N-acetylactinobolamine: some remarkably stable hemiacetals Journal of Organic Chemistry. ,vol. 52, pp. 622- 635 ,(1987) , 10.1021/JO00380A025
Gui-Bai Liang, Samuel H. Gellman, β-Turn and β-Hairpin Mimicry with Tetrasubstituted Alkenes Journal of the American Chemical Society. ,vol. 121, pp. 1806- 1816 ,(1999) , 10.1021/JA9824526
Kai Sundquist, Päivi Lakkakorpi, Björn Wallmark, Kalervo Väänänen, Inhibition of osteoclast proton transport by bafilomycin A1 abolishes bone resorption. Biochemical and Biophysical Research Communications. ,vol. 168, pp. 309- 313 ,(1990) , 10.1016/0006-291X(90)91709-2
Kenji Tonan, Kumi Adachi, Shun-ichi Ikawa, NMR study of selective H–D exchange of amide protons of d-biotin with deuterium oxide in dimethyl sulfoxide Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 54, pp. 989- 997 ,(1998) , 10.1016/S1386-1425(98)00060-2
Fritz Benz, Fritz Knüsel, Jakob Nüesch, Hansjörg Treichler, Walter Voser, Robert Nyfeler, Walter Keller-Schierlein, Stoffwechselprodukte von Mikroorganismen 143. Mitteilung. Echinocandin B, ein neuartiges Polypeptid‐Antibioticum aus Aspergillus nidulans var. echinulatus: Isolierung und Bausteine Helvetica Chimica Acta. ,vol. 57, pp. 2459- 2477 ,(1974) , 10.1002/HLCA.19740570818
Joseph M. Langenhan, John D. Fisk, Samuel H. Gellman, Evaluation of hydrogen bonding complementarity between a secondary sulfonamide and an alpha-amino acid residue. Organic Letters. ,vol. 3, pp. 2559- 2562 ,(2001) , 10.1021/OL016237X
Jeremy R. Everett, Geoffrey H. Baker, Roderick J. J. Dorgan, Novel long-range isotope effects in a macrolide antibiotic: bafilomycin A1 Journal of The Chemical Society-perkin Transactions 1. pp. 717- 724 ,(1990) , 10.1039/P29900000717