Permuting Diels-Alder and Robinson annulation stereopatterns Journal Article
| Authors: | Peng, F.; Dai, M.; Angeles, A. R.; Danishefsky, S. J. |
| Article Title: | Permuting Diels-Alder and Robinson annulation stereopatterns |
| Abstract: | Controlled isomerization of the double bond of certain Diels-Alder reaction products provides substrates that, upon oxidation, give rise to products whose gross structure corresponds to that of a Robinson annulation. In these cases, the stereochemistry of the Robinson annulation product reflects the fact that the initial combination occurred in a Diels-Alder mode. Using these principles, we have synthesized carissone and cosmosoic acid. In the latter case, our total synthesis raised serious questions as to the accuracy of the assigned structure of the natural product. © 2012 The Royal Society of Chemistry. |
| Keywords: | diels-alder reaction; total synthesis; stereochemistry; diels-alder; natural products; double bonds; robinson annulation |
| Journal Title: | Chemical Science |
| Volume: | 3 |
| Issue: | 10 |
| ISSN: | 2041-6520 |
| Publisher: | Royal Society of Chemistry |
| Date Published: | 2012-01-01 |
| Start Page: | 3076 |
| End Page: | 3080 |
| Language: | English |
| DOI: | 10.1039/c2sc20868g |
| PROVIDER: | scopus |
| PMCID: | PMC3489503 |
| PUBMED: | 23139855 |
| DOI/URL: | |
| Notes: | --- - "Export Date: 1 October 2012" - "Source: Scopus" |
Altmetric
Citation Impact
BMJ Impact Analytics
MSK Authors
-
4Angeles -
539Danishefsky
Related MSK Work