Unexpected Selectivity of Intramolecular [3+2] Cycloaddition of Trimethylenemethane (TMM) Diyl toward Total Synthesis of Conidiogenone B

Title
Unexpected Selectivity of Intramolecular [3+2] Cycloaddition of Trimethylenemethane (TMM) Diyl toward Total Synthesis of Conidiogenone B
Authors
강택김명조이상현백무현이희윤
Issue Date
2020-02
Publisher
European journal of organic chemistry
Citation
VOL 2020-617
Abstract
In the course of a study toward a total synthesis of conidiogenone B through TMM diyl-mediated tandem cycloaddition reaction, unexpected regioselectivity for a bridged isomer was observed. The synthetic and computational studies with model compounds revealed that regioselectivity can be rendered by changing substitution patterns on the TMM diyl moiety and the olefin moiety by altering the activation energy of cycloaddition reaction through a singlet TMM diyl pathway.
URI
http://pubs.kist.re.kr/handle/201004/71274
ISSN
1434-193X
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