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Approaches to the synthesis of dolastatin 11.
| dc.contributor.author | Gangwar, Sanjeev. | |
| dc.creator | Gangwar, Sanjeev. | en_US |
| dc.date.accessioned | 2011-10-31T17:56:15Z | |
| dc.date.available | 2011-10-31T17:56:15Z | |
| dc.date.issued | 1992 | en_US |
| dc.identifier.uri | http://hdl.handle.net/10150/186034 | |
| dc.description.abstract | A synthetic route to a stereoisomer of dolastatin 11, a potent antineoplastic agent from the sea hare Dolabella auricularia, is explored. Synthons for the three unusual acids were prepared as follows: (1) Hmp was prepared by a reaction used previously, but the yield was doubled and the isolation procedure greatly simplified. (2) An indirect procedure was developed for putting in the Ibu unit, with the gem-dimethyls added later. (3) Asymmetric syntheses of two Map stereoisomers established the two configurations in this unit in dolastatin 11 and in the related substances dolastatin 12, majusculamide C and 57-normajusculamide C. The nine pieces required for the 3R, 4S, 12S-stereoisomer of dolastatin 11 were assembled in a convergent synthesis to give a product which probably contains a stereoisomer of 1. An analogous route starting from the correct Map stereoisomer will very likely yield dolastatin 11 itself. | |
| dc.language.iso | en | en_US |
| dc.publisher | The University of Arizona. | en_US |
| dc.rights | Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. | en_US |
| dc.subject | Dissertations, Academic. | en_US |
| dc.subject | Chemistry, Organic. | en_US |
| dc.title | Approaches to the synthesis of dolastatin 11. | en_US |
| dc.type | text | en_US |
| dc.type | Dissertation-Reproduction (electronic) | en_US |
| dc.contributor.chair | Bates, Robert B. | en_US |
| dc.identifier.oclc | 714139808 | en_US |
| thesis.degree.grantor | University of Arizona | en_US |
| thesis.degree.level | doctoral | en_US |
| dc.contributor.committeemember | Mulvaney, James E. | en_US |
| dc.contributor.committeemember | Steelink, Cornelius | en_US |
| dc.contributor.committeemember | Enemark, John H. | en_US |
| dc.contributor.committeemember | Miller, Walter | en_US |
| dc.identifier.proquest | 9307694 | en_US |
| thesis.degree.discipline | Chemistry | en_US |
| thesis.degree.discipline | Graduate College | en_US |
| thesis.degree.name | Ph.D. | en_US |
| dc.description.note | This item was digitized from a paper original and/or a microfilm copy. If you need higher-resolution images for any content in this item, please contact us at repository@u.library.arizona.edu. | |
| dc.description.admin-note | Original file replaced with corrected file September 2023. | |
| refterms.dateFOA | 2018-08-23T08:54:05Z | |
| html.description.abstract | A synthetic route to a stereoisomer of dolastatin 11, a potent antineoplastic agent from the sea hare Dolabella auricularia, is explored. Synthons for the three unusual acids were prepared as follows: (1) Hmp was prepared by a reaction used previously, but the yield was doubled and the isolation procedure greatly simplified. (2) An indirect procedure was developed for putting in the Ibu unit, with the gem-dimethyls added later. (3) Asymmetric syntheses of two Map stereoisomers established the two configurations in this unit in dolastatin 11 and in the related substances dolastatin 12, majusculamide C and 57-normajusculamide C. The nine pieces required for the 3R, 4S, 12S-stereoisomer of dolastatin 11 were assembled in a convergent synthesis to give a product which probably contains a stereoisomer of 1. An analogous route starting from the correct Map stereoisomer will very likely yield dolastatin 11 itself. |
