Multiple chirality transfers in the enantioselective synthesis of 11-O-debenzoyltashironin. Chiroptical analysis of the key cascade Journal Article
| Authors: | Polara, A.; Cook, S. P.; Danishefsky, S. J. |
| Article Title: | Multiple chirality transfers in the enantioselective synthesis of 11-O-debenzoyltashironin. Chiroptical analysis of the key cascade |
| Abstract: | The mechanism of the cascade oxidative dearomatization-transannular Diels-Alder was investigated in the context of an asymmetric route to (-)-11-O-debenzoyltashironin. Although the oxidative dearomatization provides two acetal intermediates, the transannular Diels-Alder proceeds spontaneously from only one of the acetal isomers. Access to enantioenriched tetracyclic adduct was gained through the use of optically active allene. © 2008 Elsevier Ltd. All rights reserved. |
| Keywords: | unclassified drug; drug structure; drug synthesis; chemical structure; herbaceous agent; oxidation; acetal derivative; diels alder reaction; stereospecificity; chemical reaction; chirality; alnus; allene derivative; isomer; enantioselectivity; epimerization; aromatization; 11 o debenzoyltashironin; polarimetry; racemization; reactor cascade |
| Journal Title: | Tetrahedron Letters |
| Volume: | 49 |
| Issue: | 41 |
| ISSN: | 0040-4039 |
| Publisher: | Pergamon-Elsevier Science Ltd |
| Date Published: | 2008-10-06 |
| Start Page: | 5906 |
| End Page: | 5908 |
| Language: | English |
| DOI: | 10.1016/j.tetlet.2008.07.139 |
| PROVIDER: | scopus |
| PMCID: | PMC2598418 |
| PUBMED: | 19812682 |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 5" - "Export Date: 17 November 2011" - "CODEN: TELEA" - "Source: Scopus" |
