Studies directed toward the total synthesis of lactonamycin: Control of the sense of cycloaddition of a quinone through directed intramolecular catalysis Journal Article
| Authors: | Cox, C. D.; Siu, T.; Danishefsky, S. J. |
| Article Title: | Studies directed toward the total synthesis of lactonamycin: Control of the sense of cycloaddition of a quinone through directed intramolecular catalysis |
| Abstract: | The rapid assembly of the ABCD tetracyclic ring system of lactonamycin involved the strong-base-induced regioselective Diels-Alder reaction of 1 and 2 to form advanced precursor 3. Regiochemical control results from the suitably positioned hydroxy group, and thus only the desired isomer of 3 is obtained. |
| Keywords: | antibiotic agent; unclassified drug; drug structure; drug synthesis; anti-bacterial agents; magnetic resonance spectroscopy; quinones; molecular structure; catalysis; indoles; structure analysis; diels-alder reaction; diels alder reaction; reaction analysis; drug isolation; total synthesis; synthesis (chemical); stereochemistry; benzoquinones; cycloaddition; antibiotics; natural products; streptomyces; isomers; regioselectivity; anthracenes; aromatic compounds; article; lactonamycin; naphthoquinones |
| Journal Title: | Angewandte Chemie - International Edition |
| Volume: | 42 |
| Issue: | 45 |
| ISSN: | 1433-7851 |
| Publisher: | Wiley Blackwell |
| Date Published: | 2003-11-24 |
| Start Page: | 5625 |
| End Page: | 5629 |
| Language: | English |
| DOI: | 10.1002/anie.200352591 |
| PUBMED: | 14639734 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 12 September 2014 -- Source: Scopus |
