Tandem Double Intramolecular [4+2]/[3+2] Cycloaddition of Nitro Olefins: Part I: Construction of Piperidine Rings. Part II: Construction of Vicinal Quaternary Stereogenic Centers. Part III: Progress Toward a Total Synthesis of Daphnilactone B

The fully functionalized nitroalkene intermediate for the total synthesis of daphnilactone has also been prepared and participated in the high yielding tandem double-intramolecular [4+2]/[3+2] cycloaddition to provide a mixture of two epimeric nitroso acetals. Ozonolysis of the cycloadducts, followed by hydrogenolysis and intramolecular acylation provided the intermediates for the total synthesis that may be elaborated to daphnilactone B. Possible routes to complete the synthesis are also discussed.

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

2015

Author dc:creator

• Baiazitov, Ramil Yashnurovich

Contributors dc:contributor

• Denmark, Scott E.

• Chemistry, Organic

Language dc:language

eng

Identifier

(MiAaPQ)AAI3269837

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84254