Studies toward the total synthesis of pluraflavin A Journal Article
| Authors: | Hartung, J.; Wright, B. J. D.; Danishefsky, S. J. |
| Article Title: | Studies toward the total synthesis of pluraflavin A |
| Abstract: | A synthetic strategy towards the potent cytostatic agent pluraflavin A has been developed. Formation of the enantioenriched anthrapyran core bearing a halogen atom enabled the introduction of the α C-aryl glycoside by Stille cross-coupling and subsequent hydrogenation of the aryl glycal. Chemo- and stereoselective O-glycosylations of α oliose and β 3-epi vancosamine residues afforded a fully glycosylated aromatic core. Attempts to install the dimethylamino group of the C-disaccharide suggest that introduction of an azide group by displacement and subsequent reduction may pave the way to the total synthesis of pluraflavin A. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| Keywords: | glycosylation; sugars; synthesis (chemical); anti-cancer agents; cytostatic agents; pluraflavin a; synthetic strategies; c-glycoside; pluramycins; stille cross-coupling; subsequent reduction |
| Journal Title: | Chemistry - A European Journal |
| Volume: | 20 |
| Issue: | 28 |
| ISSN: | 0947-6539 |
| Publisher: | Wiley V C H Verlag Gmbh |
| Date Published: | 2014-07-07 |
| Start Page: | 8731 |
| End Page: | 8736 |
| Language: | English |
| DOI: | 10.1002/chem.201402254 |
| PROVIDER: | scopus |
| PUBMED: | 24919792 |
| PMCID: | PMC4795151 |
| DOI/URL: | |
| Notes: | Export Date: 1 August 2014 -- CODEN: CEUJE -- Source: Scopus |
