Asymmetric Synthesis of Dihydrospirotryprostatin B via a Silica <scp>Gel‐Mediated</scp> Cyclization of <scp>Tryptamine‐Ynamide</scp>-Reference-Cited by-同舟云学术

Asymmetric Synthesis of Dihydrospirotryprostatin B via a Silica Gel‐Mediated Cyclization of Tryptamine‐Ynamide

Published:2024-02-13 Issue:12 Volume:42 Page:1355-1359
ISSN:1001-604X
Container-title:Chinese Journal of Chemistry
language:en
Short-container-title:Chin. J. Chem.

Author:

Han Changhong¹²³,Yang Lu¹²³,Yao Kaizong¹²³,Zhang Sen¹²³,Fu Jiayue¹²³,Sun Hanyang¹²³,Xu Hongsheng⁴,Lin Bin¹²³,Cheng Maosheng¹³,Liu Yongxiang¹²³

Affiliation:

1. Key Laboratory of Structure‐Based Drug Design and Discovery of Ministry of Education Shenyang Pharmaceutical University Shenyang Liaoning 110016 China

2. Wuya College of Innovation Shenyang Pharmaceutical University Shenyang Liaoning 110016 China

3. Institute of Drug Research in Medicine Capital of China Benxi Liaoning 117000 China

4. Zhejiang Shapuaisi Pharmaceutical Co., Ltd., Pinghu Zhejiang 314299 China

Abstract

Comprehensive SummaryAn asymmetric synthesis of dihydrospirotryprostatin B was achieved in 15 steps (8 purifications) from L‐tryptophan. The main feature of our synthetic strategy is the efficient construction of spirocyclic oxindole intermediate containing a chiral quaternary carbon center, involving the silica gel‐mediated cyclization of tryptamine‐ynamide and oxidation under neat conditions.

Publisher

Wiley

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/cjoc.202300727

Reference36 articles.

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3. Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase

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