Persistent Link:
http://hdl.handle.net/10150/186034
Title:
Approaches to the synthesis of dolastatin 11.
Author:
Gangwar, Sanjeev.
Issue Date:
1992
Publisher:
The University of Arizona.
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.
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.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Dissertations, Academic.; Chemistry, Organic.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Chemistry; Graduate College
Degree Grantor:
University of Arizona
Committee Chair:
Bates, Robert B.

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titleApproaches to the synthesis of dolastatin 11.en_US
dc.creatorGangwar, Sanjeev.en_US
dc.contributor.authorGangwar, Sanjeev.en_US
dc.date.issued1992en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © 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.description.abstractA 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.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectDissertations, Academic.en_US
dc.subjectChemistry, Organic.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.contributor.chairBates, Robert B.en_US
dc.contributor.committeememberMulvaney, James E.en_US
dc.contributor.committeememberSteelink, Corneliusen_US
dc.contributor.committeememberEnemark, John H.en_US
dc.contributor.committeememberMiller, Walteren_US
dc.identifier.proquest9307694en_US
dc.identifier.oclc714139808en_US
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