Synthesis of optically pure mitomycin C: A new route to FR900482

Optically pure mitomycin C was synthesized in 28 steps and 5% overall yield from 2,6-dimethoxytoluene. The route followed was a variation upon previous work in our laboratories and the asymmetry was achieved by the resolution of racemic mitomycin A, an advanced intermediate. Our efforts at finding a new route to an intermediate in the synthesis of FR900482, are also described here. The key step was the cyclization of an epoxy-acetamide under basic conditions to form an eight-membered lactam.

Name thesis:degree_name

Master of Arts

Level thesis:degree_level

Masters

Discipline thesis:degree_discipline

Natural Sciences

Grantor

Rice University

Year dc:date.issued

1994

Author dc:creator

• Linsell, Martin Sheringham

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/1911/13860

OAI identifier oai:identifier

oai:repository.rice.edu:1911/13860