An interesting issue of Diels-Alder selectivity discovered en route to 11-O-debenzoyltashironin Journal Article
| Authors: | Cook, S. P.; Danishefsky, S. J. |
| Article Title: | An interesting issue of Diels-Alder selectivity discovered en route to 11-O-debenzoyltashironin |
| Abstract: | (Diagram presented) The hypervalent iodine-mediated oxidative dearomatization/Diels-Alder cascade was examined in the context of the natural product 11-O-debenzoyltashironin. Interestingly, the regioselectivity of the Diels-Alder reaction can be completely switched by changing the dienophile. Trapping of allyl alcohols during the oxidative dearomatization gives rise to the five-membered acetal, while trapping of allenyl alcohols results in the six-membered acetal. © 2006 American Chemical Society. |
| Keywords: | unclassified drug; chemistry; aldehydes; oxidation reduction reaction; oxidation-reduction; synthesis; indicators and reagents; iodine; bridged compounds; aldehyde; bicyclo compound; 11 o debenzoyltashironin; dyes, reagents, indicators, markers and buffers; bicyclo compounds; 11-o-debenzoyltashironin; alcohol derivative; bridged compound; alcohols |
| Journal Title: | Organic Letters |
| Volume: | 8 |
| Issue: | 25 |
| ISSN: | 1523-7060 |
| Publisher: | American Chemical Society |
| Date Published: | 2006-12-07 |
| Start Page: | 5693 |
| End Page: | 5695 |
| Language: | English |
| DOI: | 10.1021/ol062067i |
| PUBMED: | 17134249 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 19" - "Export Date: 4 June 2012" - "Source: Scopus" |
