Enantioselective syntheses of heteroyohimbine natural products: A unified approach through cooperative catalysis

Ashkaan Younai; Bi Shun Zeng; Herbert Y. Meltzer; Karl A. Scheidt

doi:10.1002/anie.201502011

Enantioselective syntheses of heteroyohimbine natural products: A unified approach through cooperative catalysis

Ashkaan Younai, Bi Shun Zeng, Herbert Y. Meltzer, Karl A. Scheidt^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to as "anhydronium bases") containing three contiguous stereocenters. Each possesses interesting biological activity, with alstonine being the major component of a plant-based remedy to treat psychosis and other nervous system disorders. This work describes the enantioselective total syntheses of these natural products with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step. The enantioselective total syntheses of the natural products alstonine and serpentine are presented. They proceed through a sequence with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.

Original language	English (US)
Pages (from-to)	6900-6904
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	54
Issue number	23
DOIs	https://doi.org/10.1002/anie.201502011
State	Published - Jun 1 2015

Keywords

cooperative catalysis
enamine catalysis
enantioselectivity
schizophrenia
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201502011

Cite this

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title = "Enantioselective syntheses of heteroyohimbine natural products: A unified approach through cooperative catalysis",

abstract = "Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to as {"}anhydronium bases{"}) containing three contiguous stereocenters. Each possesses interesting biological activity, with alstonine being the major component of a plant-based remedy to treat psychosis and other nervous system disorders. This work describes the enantioselective total syntheses of these natural products with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step. The enantioselective total syntheses of the natural products alstonine and serpentine are presented. They proceed through a sequence with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.",

keywords = "cooperative catalysis, enamine catalysis, enantioselectivity, schizophrenia, total synthesis",

author = "Ashkaan Younai and Zeng, {Bi Shun} and Meltzer, {Herbert Y.} and Scheidt, {Karl A.}",

year = "2015",

month = jun,

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doi = "10.1002/anie.201502011",

language = "English (US)",

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journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

number = "23",

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T1 - Enantioselective syntheses of heteroyohimbine natural products

T2 - A unified approach through cooperative catalysis

AU - Younai, Ashkaan

AU - Zeng, Bi Shun

AU - Meltzer, Herbert Y.

AU - Scheidt, Karl A.

PY - 2015/6/1

Y1 - 2015/6/1

N2 - Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to as "anhydronium bases") containing three contiguous stereocenters. Each possesses interesting biological activity, with alstonine being the major component of a plant-based remedy to treat psychosis and other nervous system disorders. This work describes the enantioselective total syntheses of these natural products with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step. The enantioselective total syntheses of the natural products alstonine and serpentine are presented. They proceed through a sequence with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.

AB - Alstonine and serpentine are pentacyclic indoloquinolizidine alkaloids (referred to as "anhydronium bases") containing three contiguous stereocenters. Each possesses interesting biological activity, with alstonine being the major component of a plant-based remedy to treat psychosis and other nervous system disorders. This work describes the enantioselective total syntheses of these natural products with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step. The enantioselective total syntheses of the natural products alstonine and serpentine are presented. They proceed through a sequence with a cooperative hydrogen bonding/enamine-catalyzed Michael addition as the key step.

KW - cooperative catalysis

KW - enamine catalysis

KW - enantioselectivity

KW - schizophrenia

KW - total synthesis

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DO - 10.1002/anie.201502011

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Enantioselective syntheses of heteroyohimbine natural products: A unified approach through cooperative catalysis

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 1040072: Experimental Crystal Structure Determination

CCDC 1030168: Experimental Crystal Structure Determination

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Enantioselective syntheses of heteroyohimbine natural products: A unified approach through cooperative catalysis

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

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Datasets

CCDC 1040072: Experimental Crystal Structure Determination

CCDC 1030168: Experimental Crystal Structure Determination

Cite this