Total synthesis of (−)-amathaspiramide A <i>via</i> a one-pot aldol addition/transamidification reaction-Reference-Cited by-同舟云学术

Total synthesis of (−)-amathaspiramide A via a one-pot aldol addition/transamidification reaction

Published:2022 Issue:11 Volume:9 Page:3045-3049
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Wang Jun-Jie¹,Bai Rui-Xue²,Yang Mao-Qi¹,Chen Zheng-Yu¹,Wang Min-Dan¹,Zhao Qian¹,Lin Guo-Qiang¹²,Fu Jian-Guo¹^ORCID,Feng Chen-Guo¹²

Affiliation:

1. The Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, China

2. Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, China

Abstract

Total synthesis of (−)-amathaspiramide A was achieved through efficient construction of a chiral aza-spirobicyclic core using an aldol addition/transamidification cascade. Configuration adjustment via an asymmetric protonation process was used to obtain the stereochemistry.

Funder

Science and Technology Commission of Shanghai Municipality

Shanghai Municipal Education Commission

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2022/QO/D2QO00032F

Reference36 articles.

1. Amathaspiramides A−F, Novel Brominated Alkaloids from the Marine Bryozoan Amathia wilsoni

2. Antiproliferative Activity of Amathaspiramide Alkaloids and Analogs

3. The Total Synthesis of (−)-Amathaspiramide F

4. Total Synthesis of (−)-Amathaspiramide F

5. Synthesis of (±)-Amathaspiramide F and Discovery of an Unusual Stereocontrolling Element for the [2,3]-Stevens Rearrangement