Synthesis of the functionalized tricyclic skeleton of guanacastepene A: A tandem epoxide-opening β-elimination/knoevenagel cyclization Journal Article
| Authors: | Tan, D. S.; Dudley, G. B.; Danishefsky, S. J. |
| Article Title: | Synthesis of the functionalized tricyclic skeleton of guanacastepene A: A tandem epoxide-opening β-elimination/knoevenagel cyclization |
| Abstract: | Some serious and unexpected complications emerged in the key annulation step required to reach 1, the core of guanacastepene A (see scheme). The solution to these problems concurrently solved the major issues associated with the different oxidation states of C14 and C15. Although the authors have not generalized this type of annulation, it could have broad applications to building incrementally oxygenated polycyclic natural products. |
| Keywords: | unclassified drug; drug structure; molecular structure; conformation; cyclization; structure analysis; oxidation; synthesis; total synthesis; synthesis (chemical); stereochemistry; diterpene; epoxy compounds; antibiotics; diterpenes; natural products; aromatic compounds; guanacastepene a; article; annulations |
| Journal Title: | Angewandte Chemie - International Edition |
| Volume: | 41 |
| Issue: | 12 |
| ISSN: | 1433-7851 |
| Publisher: | Wiley Blackwell |
| Date Published: | 2002-06-17 |
| Start Page: | 2185 |
| End Page: | 2188 |
| Language: | English |
| DOI: | 10.1002/1521-3773(20020617)41:12<2185::aid-anie2185>3.0.co;2-0 |
| PUBMED: | 19746639 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 14 November 2014 -- Source: Scopus |
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