Synthetic Studies Towards the Core Structure of Nakadomarin A by a Thioamide‐Based Strategy
作者： Jai K. Chavda , Panayiotis A. Procopiou , Peter N. Horton , Simon J. Coles , Michael J. Porter
关键词:
摘要: The tricyclic BCD substructure of the marine natural product nakadomarin A has been synthesised. strategy utilised a key carbon–carbon bond-forming reaction between furan and an N-acyliminium ion derived from secondary thiolactam. In addition, novel three-component coupling thioamide, allylic bromide isocyanate, leading to establishment two new stereogenic centres, is reported.
science-open.com 参考文章(54)
Simone Bonazzi, Bichu Cheng, Joseph S. Wzorek, David A. Evans, Total Synthesis of (−)-Nakadomarin A Journal of the American Chemical Society. ,vol. 135, pp. 9338- 9341 ,(2013) , 10.1021/JA404673S
Y. Tamaru, M. Mizutani, Y. Furukawa, O. Kitao, Z. Yoshida, Stereoselective generation of Z-ketene S,N-acetal from S-alkyl onium salt of thioamide and its application to diastereoselective α-allylation of thioamide Tetrahedron Letters. ,vol. 23, pp. 5319- 5322 ,(1982) , 10.1016/S0040-4039(00)85828-1
Fuyuhiko Inagaki, Masahiko Kinebuchi, Naoki Miyakoshi, Chisato Mukai, Formal synthesis of (+)-nakadomarin A. Organic Letters. ,vol. 12, pp. 1800- 1803 ,(2010) , 10.1021/OL100412F
John K. Thottathil, Jerome L. Moniot, Richard H. Mueller, Michael K. Y. Wong, Thomas P. Kissick, Conversion of L-pyroglutamic acid to 4-alkyl-substituted L-prolines. The synthesis of trans-4-cyclohexyl-L-proline Journal of Organic Chemistry. ,vol. 51, pp. 3140- 3143 ,(1986) , 10.1021/JO00366A011
Scott M. Sheehan, L. Scott Beall, Albert Padwa, π-Cyclization reactions of thio N-acyliminium ions for heterocyclic synthesis Tetrahedron Letters. ,vol. 39, pp. 4761- 4764 ,(1998) , 10.1016/S0040-4039(98)00902-2
J. Kobayashi, M. Tsuda, Masami Ishibashi, Bioactive products from marine micro- and macro-organisms* Pure and Applied Chemistry. ,vol. 71, pp. 1123- 1126 ,(1999) , 10.1351/PAC199971061123
Hiroki Takahata, Akira Tomiguchi, Masaharu Nakano, Takao Yamazaki, Activated Lactams: A One-Step Synthesis of Azacycloalka[2,3d]pyrimidine Derivatives using Ketene-S,Nacetals Synthesis. ,vol. 1982, pp. 156- 157 ,(1982) , 10.1055/S-1982-29728
Alois Fürstner, Oliver Guth, Antonio Rumbo, Günter Seidel, Ring Closing Alkyne Metathesis. Comparative Investigation of Two Different Catalyst Systems and Application to the Stereoselective Synthesis of Olfactory Lactones, Azamacrolides, and the Macrocyclic Perimeter of the Marine Alkaloid Nakadomarin A Journal of the American Chemical Society. ,vol. 121, pp. 11108- 11113 ,(1999) , 10.1021/JA992074K
Jens Christoffers, Heiko Oertling, Peter Fischer, Wolfgang Frey, Studies on the α-acetylation of δ-valerolactone and ε-caprolactone Tetrahedron. ,vol. 59, pp. 3769- 3778 ,(2003) , 10.1016/S0040-4020(03)00511-8
M. J. BEARD, J. H. BAILEY, D. T. CHERRY, M. G. MOLONEY, S. B. SHIM, K. A. STATHAM, M. J. BAMFORD, R. B. LAMONT, Functionalized Pyrrolidinones Derived from (S)-Pyroglutamic Acid. ChemInform. ,vol. 27, ,(1996) , 10.1002/CHIN.199627149