Stereoselective Protection-Free Asymmetric Total Synthesis of (+)-Chamuvarinin, a Potent Anticancer and Antitrypanosomal Agent: Substrate-Controlled Construction of the Adjacently Linked Oxatricyclic Core by Internal Alkylation

A stereoselective protection-free asymmetric total synthesis of (+)-chamuvarinin (1), a potent anticancer and antitrypanosomal agent, has been accomplished. The adjacently linked [bis­(tetrahydrofuran)]­tetrahydropyran (THF–THF–THP) core of this natural product with seven stereogenic centers was con...

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Bibliographic Details
Published in:Organic letters 2018-10, Vol.20 (20), p.6398-6402
Main Authors: Samala, Mallesham, Lu, Thien Nhan, Mandava, Suresh, Hwang, Jungjoong, Bogonda, Ganganna, Kim, Donghoon, Park, Haeil, Kim, Deukjoon, Lee, Jongkook
Format: Article
Language:English
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Summary:A stereoselective protection-free asymmetric total synthesis of (+)-chamuvarinin (1), a potent anticancer and antitrypanosomal agent, has been accomplished. The adjacently linked [bis­(tetrahydrofuran)]­tetrahydropyran (THF–THF–THP) core of this natural product with seven stereogenic centers was constructed in a completely substrate-controlled fashion. The inter-ring stereochemistry (threo,threo,threo) of the oxatricyclic core was established in a stereoselective fashion by a chelation-controlled Keck allylation, whereas the intraring cis or trans relative stereochemistry was controlled by a stereoselective internal alkylation.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02706