Reinventing the wheel for enabling the synthesis of hinckdentine A

[Display omitted] •A summary of synthetic routes toward hinckdentine A was given.•The key reactions featured in total syntheses were highlighted.•A tentative biogenesis of hinckdentine A was also suggested. A documented synthetic method, even a sophisticated one, is not always inornate and viable fo...

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Bibliographic Details
Published in:Tetrahedron letters 2021-03, Vol.67, p.152880, Article 152880
Main Authors: Ruan, Zhuwei, Zhu, Lili, Zheng, Kuan, Hong, Ran
Format: Article
Language:English
Subjects:
Biogenesis
Cyclization
Indole alkaloid
Synthetic method
Total synthesis
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Summary:[Display omitted] •A summary of synthetic routes toward hinckdentine A was given.•The key reactions featured in total syntheses were highlighted.•A tentative biogenesis of hinckdentine A was also suggested. A documented synthetic method, even a sophisticated one, is not always inornate and viable for synthesizing novel compounds due to the obscured compatibility with the reactivity of specific functional groups. With a unique indolo[1,2-c]quinazoline framework, hinckdentine A has provoked renewed interest in the scientific community for the opportunity to develop new synthetic methods and strategies. Four groups have completed the total synthesis of hinckdentine A with distinct approaches enabled by improving the Pinacol-type rearrangement, base-promoted stereospecific alkyl migration, the intramolecular Heck reaction, the aryne-initiated cascade reaction, and electrolytic radical cyclization. The tentative biogenesis of hinckdentine A has been proposed to inspire future development of efficient synthesis and biosynthetic study.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.152880