TOWARDS THE TOTAL SYNTHESIS OF 7-<em>EPI</em>-CLUSIANONE

• Main Author: Dutta, Shubhankar
• Format: Others
• Published: UKnowledge 2017
• Subjects: Polycyclic polyprenylated acylphloroglucinols; 7-epi-clusianone; bicyclo[3.3.1]nonane; 2-alkenone; β-hydroxy 2-alkenone; Organic Chemistry
• Online Access: http://uknowledge.uky.edu/chemistry_etds/79; http://uknowledge.uky.edu/cgi/viewcontent.cgi?article=1088&amp;context=chemistry_etds

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.