Exploring Short and Efficient Synthetic Routes Using Titanocene(III)-Catalyzed Reactions: Total Synthesis of Natural Meroterpenes with Trisubstituted Unsaturations

The stereo- and regioselective total syntheses of OMe derivatives of the scarce bioactive meroterpenoids makassaric acid ( ) and fascioquinol B ( ) have been accomplished. The synthetic sequences are based on the following three efficient and selective catalytic reactions: Cu-catalyzed addition of G...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2022-04, Vol.27 (8), p.2400
Main Authors: Rosales, Jennifer, Cabrera, Gustavo, Justicia, José
Format: Article
Language:English
Subjects:
Acids
Catalysis
Chemical reactions
Cyclization
natural product
Organic chemistry
Organometallic Compounds
Product development
radicals
Regioselectivity
Stereoisomerism
Stereoselectivity
synthetic methods
terpenes
titanocene
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Summary:The stereo- and regioselective total syntheses of OMe derivatives of the scarce bioactive meroterpenoids makassaric acid ( ) and fascioquinol B ( ) have been accomplished. The synthetic sequences are based on the following three efficient and selective catalytic reactions: Cu-catalyzed addition of Grignard compounds to an epoxide; a regioselective Barbier-type reaction, catalyzed by Cp TiCl; and regio- and stereoselective bioinspired cyclization, also catalyzed by Cp TiCl. These three key processes allow us to obtain the main skeletons of and in a few steps. The valuable synthetic proposal shown in this work provides fast access to scarce, structurally complex meroterpenes with promising biological activities, which are a sustainable source for later studies and applications in medicine.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27082400