Year of Publication
Doctor of Philosophy (PhD)
Arts and Sciences
Dr. Robert B. Grossman
Polycyclic polyprenylated acylphloroglucinols (PPAPs) are plant- (Guttiferae) derived natural products. They have fascinating bicyclo[3.3.1]nonane-2,4,9-trione or [3.2.1]nonane-2,4,8-trione cores decorated with prenyl or geranyl groups. More than 200 PPAPs have been isolated, but only a few of them have been synthesized, although most of the synthesized PPAPs are of type A and have an exo substituent at C (7). Here, we are trying to make a type B 7-endo PPAP, 7-epi-clusianone. The synthetic plan involves an alkynylation–aldol strategy to construct the bicyclic core. Having established the bicyclic core, the synthesis presents a new challenge: the oxidation of a very hindered 2-alkenone to the β-hydroxy 2-alkenone.
Digital Object Identifier (DOI)
Dutta, Shubhankar, "TOWARDS THE TOTAL SYNTHESIS OF 7-EPI-CLUSIANONE" (2017). Theses and Dissertations--Chemistry. 79.