Catalytic Enantioselective Nitrone Cycloadditions Enabling Collective Syntheses of Indole Alkaloids

Overview

Journal Nat Commun

Specialty Biology

Date 2024 Jul 30

PMID 39080291

Authors

Xiaochen Tian

Tengfei Xuan

Jingkun Gao

Xinyu Zhang

Tao Liu

Fengbiao Luo

Ruochen Pang

Pengcheng Shao

Yun-Fang Yang

Yang Wang

Affiliations

Soon will be listed here.

Abstract

Tetrahydro-β-carboline skeletons are prominent and ubiquitous in an extraordinary range of indole alkaloid natural products and pharmaceutical compounds. Powerful synthetic approaches for stereoselective synthesis of tetrahydro-β-carboline skeletons have immense impacts and have attracted enormous attention. Here, we outline a general chiral phosphoric acid catalyzed asymmetric 1,3-dipolar cycloaddition of 3,4-dihydro-β-carboline-2-oxide type nitrone that enables access to three types of chiral tetrahydro-β-carbolines bearing continuous multi-chiral centers and quaternary chiral centers. The method displays different endo/exo selectivity from traditional nitrone chemistry. The distinct power of this strategy has been illustrated by application to collective and enantiodivergent total syntheses of 40 tetrahydro-β-carboline-type indole alkaloid natural products with divergent stereochemistry and varied architectures.

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