Seven-step total synthesis of α-cyclopiazonic acid

A seven-step total synthesis of α-cyclopiazonic acid was achieved via a bioinspired [3 + 2] annulation to form the C/D rings. [Display omitted] A seven-step total synthesis of α-cyclopiazonic acid is reported from a commercially available 4-bromoindole. Salient feature of the work is the rapid forma...

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Bibliographic Details
Published inChinese chemical letters Vol. 31; no. 2; pp. 401 - 403
Main Authors Shi, Shibin, Yuan, Kuo, Jia, Yanxing
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier B.V 01.02.2020
Elsevier
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
Subjects
Cascade cyclization
Chemistry
Chemistry, Multidisciplinary
Indole alkaloids
Natural products
Physical Sciences
Science & Technology
Total synthesis
Cascade cyclization
Natural products
Indole alkaloids
Total synthesis
ENANTIOSELECTIVE SYNTHESIS
ASPERGILLUS-FLAVUS
ALKALOIDS
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Summary:A seven-step total synthesis of α-cyclopiazonic acid was achieved via a bioinspired [3 + 2] annulation to form the C/D rings. [Display omitted] A seven-step total synthesis of α-cyclopiazonic acid is reported from a commercially available 4-bromoindole. Salient feature of the work is the rapid formation of tetracyclic skeleton via a bioinspired [3 + 2] annulation to form the C/D rings.
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2019.06.048