Total Synthesis of Aegyptinones A and B ; Synthetic Approaches to Glycinoeclepin A PDF Download
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Author: Alexandre Henri Huboux
Publisher:
ISBN:
Category :
Languages : en
Pages : 520
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Book Description
Author: Alexandre Henri Huboux
Publisher:
ISBN:
Category :
Languages : en
Pages : 520
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Book Description
Author:
Publisher:
ISBN:
Category : Dissertation abstracts
Languages : en
Pages : 800
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Book Description
Author:
Publisher:
ISBN:
Category : Dissertations, Academic
Languages : en
Pages : 780
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Book Description
Author: Chauncey Dale Jones
Publisher:
ISBN:
Category :
Languages : en
Pages : 92
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Book Description
Two synthetic approaches toward the synthesis of an analog that would mimic the activity of glycinoeclepin A are described. The analog was made in accordance to studies done by Murai and Kraus. In Murai's studies it was determined the carboxyl group and hydroxyl group on the C ring and the carboxyl group on the D ring of glycinoeclepin A are essential for activity. The cross-conjugated system in the C ring is not critical for activity. With these studies in mind, we set out to develop a synthesis that would be cost effective, short, and hold the key components for activity. In our first approach we focused on chemistry starting with 3-methoxyphenylacetonitrile. The key steps of the route were a Birch reduction, acid hydrolysis, and an aldol condensation. However, after numerous attempts to effect the aldol condensation, we changed our focus to a more convergent approach. In the second approach we synthesized our target analog via a new carbanion-based strategy, which put a functionalized six-membered ring onto a ketone. This new annulation process may prove effective in the synthesis of other natural products.
