Authors: Stiasni, Nikola
Title: Synthetic studies toward the total synthesis of berkelic acid and lytophilippine A
Language (ISO): en
Abstract: C16-C20 part of natural product berkelic acid containing two adjacent stereogenic centers has been synthesized employing catalytic asymmetric Gosteli-Claisen rearrangement of 2 alkoxycarbonyl-substituted allyl vinyl ether as a key step. Synthetic sequence leading to the both fragments included 11 linear steps and afforded final products in good to excellent diastereoselectivity and good enantioselectivity. Model study exploring Oxa-Pictet-Spengler condensation as a key coupling step toward the tetracyclic core of berkelic acid has been successfully accomplished. C20-C27 fragment of lytophilippine A has been synthesized in a sequence of 13 linear steps, and in total yield of 8.4%. The synthesis commenced with readily available natural (+) L ascorbic acid and features Evans asymmetric alkylation and asymmetric aldol condensation with norephedrine-derived auxiliary as key steps to install the required C21-C23 anti, syn stereotriad.
Subject Headings: Berkelic acid
Lytophilippine A
URI: http://hdl.handle.net/2003/27643
http://dx.doi.org/10.17877/DE290R-8830
Issue Date: 2011-03-08
Appears in Collections:Organische Chemie

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