Asymmetric synthesis of (−)-sedacryptine through a diastereoselective Mannich reaction of N,O-acetals with ketones-Reference-Cited by-同舟云学术

Asymmetric synthesis of (−)-sedacryptine through a diastereoselective Mannich reaction of N,O-acetals with ketones

Published:2018 Issue:5 Volume:16 Page:771-779
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Liu Yi-Wen¹²³⁴,Ma Rui-Jun⁵⁶⁷⁴,Yan Jia-Hang¹²³⁴,Zhou Zhu¹²³⁴,Wei Bang-Guo¹²³⁴^ORCID

Affiliation:

1. Institutes of Biomedical Sciences and School of Pharmacy

2. Fudan University

3. Shanghai

4. China

5. Center for Gastrointestinal Endoscopy

6. Shanxi Provincial People's Hospital

7. Taiyuan 030012

Abstract

An approach to access the 3-hydroxyl-2,6-disubstituted piperidine scaffold has been developed through the Mannich process involving N,O-acetals and ketones, and the process is demonstrated by the asymmetric synthesis of (−)-sedacryptine.

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2018/OB/C7OB02989F

Reference63 articles.

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3. Recent Progress in the Synthesis of 2,6-Disubstituted Hydroxypiperidine Alkaloids

4. Enantiocontrolled Synthesis of 2,3,6-Trisubstituted Piperidines Using (η3-Dihydropyridinyl)molybdenum Complexes as Chiral Scaffolds. Total Synthesis of (−)-Indolizidine 209B

5. Diastereoselective Reduction of Bicyclic -Enamino Carbonyl Piperidines – Application to the Total Synthesis of (–)-Deoxocassine

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