PHOTOCHEMICAL HYDROXYLATION OF 1-METHYLANTHRAQUINONES: SYNTHESIS OF 9`-HYDROXYALOESAPONARIN II

Triplet excited 9,10-anthraquinones can abstract H from alkyl groups ortho to the carbonyl. The hydrogen transfer results in a 1,x biradical which then undergoes a variety of reactions. One of these, oxidation of an alkyl substituent ortho to one of the carbonyls, was believed to go through formation of an endoperoxide. Photolysis of 1-methyl-9,10-anthraquinones using 419 nm light gave the corresponding suggested endoperoxide cleanly, supporting the hypothesis. Reduction of the endoperoxide resulted in oxidation of the ortho methyl group. The scope of the reaction was examined by using the photochemical hydroxylation in the first synthesis of a natural product, 9'-hydroxyaloesaponarin II.

Grantor dc:publisher

Wake Forest University

Year dc:date.issued

2012

Author dc:creator

• Elkazaz, Salwa Salah

• Anthracene

Language dc:language.iso

en

Handle dc:identifier.uri

http://hdl.handle.net/10339/37426

OAI identifier oai:identifier

oai:wakespace.lib.wfu.edu:10339/37426