The total synthesis of eleutherobin Journal Article
| Authors: | Chen, X. T.; Bhattacharya, S. K.; Zhou, B.; Gutteridge, C. E.; Pettus, T. R. R.; Danishefsky, S. J. |
| Article Title: | The total synthesis of eleutherobin |
| Abstract: | The total synthesis of the title compound (1), starting with (R)-(-)- α-phellandrene (6), has been accomplished. The synthesis rigorously proves the relative stereochemical relationship of the diterpenoid and carbohydrate domains of eleutherobin. Key reactions included a Nozaki-Kishi ring closure to produce a furanophane (see 37→38), a pyranose to furanose transposition (see 50 → 47), and a novel oxycarbaglycosidation (cf. 58 → 87) for joining the two domains. |
| Keywords: | unclassified drug; paclitaxel; drug structure; drug synthesis; cyclization; natural product; oxidation; reaction analysis; chemical reaction; stereochemistry; acylation; discodermolide; article; eleuterobin; sarcodictyin a |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 121 |
| Issue: | 28 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 1999-07-21 |
| Start Page: | 6563 |
| End Page: | 6579 |
| Language: | English |
| DOI: | 10.1021/ja990215c |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Article -- Export Date: 16 August 2016 -- Source: Scopus |
