Catalytic Enantioselective Formal Synthesis of MDM2 Antagonist RG7388 and Its Analogues

Summary of main observation and conclusion The catalytic asymmetric 1,3‐dipolar [3 + 2] cycloaddition of azomethine ylides with stilbenes has been established, affording structurally diverse pyrrolidines bearing four contiguous stereocenters with stereo‐diversity in generally high yields and good to...

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Bibliographic Details
Published inChinese journal of chemistry Vol. 38; no. 5; pp. 435 - 438
Main Authors Zou, Xue‐Jie, Yang, Wu‐Lin, Zhu, Jing‐Yan, Deng, Wei‐Ping
Format Journal Article
LanguageEnglish
Published Weinheim WILEY‐VCH Verlag GmbH & Co. KGaA 01.05.2020
Wiley
Wiley Subscription Services, Inc
Subjects
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Cycloaddition
Enantiomers
MDM2 protein
Physical Sciences
Science & Technology
ASYMMETRIC 1,3-DIPOLAR CYCLOADDITION
PRACTICAL SYNTHESIS
HETEROCYCLES
CONSTRUCTION
AZOMETHINE YLIDES
FRAMEWORK
INHIBITORS
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Summary:Summary of main observation and conclusion The catalytic asymmetric 1,3‐dipolar [3 + 2] cycloaddition of azomethine ylides with stilbenes has been established, affording structurally diverse pyrrolidines bearing four contiguous stereocenters with stereo‐diversity in generally high yields and good to excellent stereoselectivities (up to 98% yield, 99 : 1 dr, >99% ee). Meanwhile, this strategy allowed the formal synthesis of antitumor drug RG7388 (Phase III clinical study) and its analogues in high efficiency. Copper(I)‐catalyzed asymmetric 1,3‐dipolar [3 + 2] cycloaddition between stilbenes and azomethine ylides was established, affording RG7388 precursor and its analogues in high yields with high diastereo‐ and enantioselectivities.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201900530