A highly stereoselective total synthesis of hispidospermidin: Derivation of a pharmacophore model Journal Article
| Authors: | Frontier, A. J.; Raghavan, S.; Danishefsky, S. J. |
| Article Title: | A highly stereoselective total synthesis of hispidospermidin: Derivation of a pharmacophore model |
| Abstract: | The total synthesis of the title compound has been accomplished. Among the key steps were (i) a conjugate addition - Robinson annulation - type sequence (see 4), (ii) intramolecular carbomercuration (see 3), (iii) a reduction-ketonization sequence (see 25), (iv) cycloetherification of an unactivated methylene group (see 28), and reductive amination (see 1). A highly preliminary SAR profile suggests that the functional cytotoxic pharmacophore of hispidospermidin involved a presentation of spermidine derivative 36 via linkage to a ball-like hydrophobic cage to its target. |
| Keywords: | unclassified drug; cytotoxicity; structure activity relation; chemical structure; pharmacophore; amination; cyclization; natural product; model; reaction analysis; synthesis; stereochemistry; derivatization; ketone; reduction; hydrophobicity; article; hispidospermidin; spermidine derivative |
| Journal Title: | Journal of the American Chemical Society |
| Volume: | 122 |
| Issue: | 26 |
| ISSN: | 0002-7863 |
| Publisher: | American Chemical Society |
| Date Published: | 2000-07-05 |
| Start Page: | 6151 |
| End Page: | 6159 |
| Language: | English |
| DOI: | 10.1021/ja9944960 |
| PROVIDER: | scopus |
| DOI/URL: | |
| Notes: | Export Date: 18 November 2015 -- Source: Scopus |
