A total synthesis of xestodecalactone A and proof of its absolute stereochemistry: Interesting observations on dienophilic control with 1,3-disubstituted nonequivalent allenes Journal Article
| Authors: | Yoshino, T.; Ng, F.; Danishefsky, S. J. |
| Article Title: | A total synthesis of xestodecalactone A and proof of its absolute stereochemistry: Interesting observations on dienophilic control with 1,3-disubstituted nonequivalent allenes |
| Abstract: | A concise total synthesis of xestodecalactone A, utilizing a Diels-Alder strategy is described. The focal Diels-Alder reaction relied on an "ynoate" dienophile to rapidly assemble the required resorcylinic acid scaffold. During this study, Diels-Alder cycloaddition reactions involving 1,3-disubstituted nonequivalent allene dienophiles were studied, and some surprising results were encountered. © 2006 American Chemical Society. |
| Keywords: | unclassified drug; chemical structure; cyclization; structure analysis; olefins; diels alder reaction; reaction analysis; chemical reaction; synthesis; synthesis (chemical); stereochemistry; stereoisomerism; ketones; chemical bond; lactone derivative; cycloaddition; lactones; aromatic compound; allene derivative; alkadienes; substitution reactions; assembly; diels-alder strategy; dienophilic control; resorcylinic acid; xestodecalactone; resocylinic acid; xestodecalactone a |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 128 |
| Issue: | 43 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2006-11-01 |
| Start Page: | 14185 |
| End Page: | 14191 |
| Language: | English |
| DOI: | 10.1021/ja064270e |
| PUBMED: | 17061903 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | --- - "Cited By (since 1996): 24" - "Export Date: 4 June 2012" - "CODEN: JACSA" - "Source: Scopus" |
