A Convergent Route for the Total Synthesis of Malyngamides O, P, Q, and R
| Autor: | Jie Chen, Xian-Liang Qi, Xiaogang Fu, Xiao-Ping Cao, Ling Zhou, Jun-Tao Zhang |
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| Rok vydání: | 2009 |
| Předmět: |
Biological Products
Chemistry Stereochemistry Organic Chemistry Vinyl Chloride Enantioselective synthesis Absolute configuration Total synthesis Stereoisomerism Alkenes Amides Chemical synthesis Vinyl chloride chemistry.chemical_compound Wittig reaction Pyrroles Mitsunobu reaction Epimer Acids Acyclic |
| Zdroj: | The Journal of Organic Chemistry. 74:4149-4157 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo9003103 |
| Popis: | A convergent, enantioselective and general synthetic route to a class of marine natural products-malyngamides O (1), P (2), Q (3), R (4), 5''-epi-3 and 5''-epi-4-bearing a novel vinyl chloride structural motif was developed. The key steps involved construction of the vinyl chloride functionality by Wittig reaction, a DCC/HOBt-promoted amidation, an aldol reaction in the construction of the basic backbone of 1, 2, 3, 4, 5''-epi-3, and 5''-epi-4, and methylation of an enol moiety via either base/acid conditions or a Mitsunobu reaction. Moreover, the absolute configuration of the stereogenic center at C-5'' in 3 was further confirmed by synthesis of the natural product and its C-5'' epimer. |
| Databáze: | OpenAIRE |
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