Approaches to the Synthesis of the Ophiobolin Ring System

The ophiobolin and ceroplastol sesterterpenes have been isolated from a variety of different insects and microorganisms. The unusual structures and biological activities of these compounds have prompted us to undertake studies directed towards their total synthesis. The synthetic plan involved the application of an intramolecular photocycloaddition reaction of (DELTA)('(alpha),(beta))-butenolide derivatives and the reductive cleavage of the derived cyclobutanes. This procedure provides a novel method for effecting two-carbon ring expansion.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Senter, Peter Dana

• Chemistry, Organic

Identifier

(UMI)AAI8203585

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70173