A novel aldol condensation with 2-methyl-4-pentenal and its application to an improved total synthesis of epothilone B Journal Article
| Authors: | Balog, A.; Harris, C.; Savin, K.; Zhang, X. G.; Chou, T. C.; Danishefsky, S. J. |
| Article Title: | A novel aldol condensation with 2-methyl-4-pentenal and its application to an improved total synthesis of epothilone B |
| Abstract: | The stabilization of the transition state through a favorable interaction between the double bond of 1 and the carbonyl group of 2 appears to be responsible for the high diastereoface selectivity of the aldol reaction. This key step in the highly concise total synthesis of epothilone B is followed by a Suzuki coupling to introduce the thiazole domain, a Noyori reduction to control the stereochemistry at C3, and a final macrolactonization (see reaction scheme). X = protecting group. |
| Keywords: | total synthesis; epothilones; natural products; aldol reactions; suzuki coupling |
| Journal Title: | Angewandte Chemie - International Edition |
| Volume: | 37 |
| Issue: | 19 |
| ISSN: | 1433-7851 |
| Publisher: | Wiley Blackwell |
| Date Published: | 1998-10-16 |
| Start Page: | 2675 |
| End Page: | 2678 |
| Language: | English |
| DOI: | 10.1002/(sici)1521-3773(19981016)37:19<2675::aid-anie2675>3.0.co;2-o |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 12 December 2016 -- Source: Scopus |
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