Total synthesis of (-)-tantazole B. Total synthesis of (+,-)-FR900482

Tantazole B is a newly isolated tolytoxin. FR900482 is a recently isolated potent antitumor antibiotic. They both have novel structural features which present challenges to the synthetic chemists. The first total synthesis and structure revision of ($-$)-tantazole B is described herein. A convergent methodology is developed and could be applied to the synthesis of the other members of oxazole/thiazoline family.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI) The first and, to date, only total synthesis of $(\pm)$-FR900482 is also described here. The stereocontrolled total synthesis of FR900482 features a facile construction of the 8-membered intermediate through reductive amination, stereospecific hydroxymethyla-tion and efficient oxidation of the amine to the hydroxylamine.

Name thesis:degree_name

Doctor of Philosophy

Level thesis:degree_level

Doctoral

Discipline thesis:degree_discipline

Natural Sciences

Grantor

Rice University

Year dc:date.issued

1993

Author dc:creator

• Xu, Lianhong

Advisor dc:contributor.advisor

• Fukuyama, Tohru

• Organic chemistry

Statement dc:rights

• Copyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.

Language dc:language.iso

eng

Handle dc:identifier.uri

https://hdl.handle.net/1911/16691

OAI identifier oai:identifier

oai:repository.rice.edu:1911/16691