Concise Asymmetric Total Synthesis of ent-Ancistrocladinium A

Kyung Hee Kim; Cheol Hong Cheon

doi:10.1002/adsc.201600472

Concise Asymmetric Total Synthesis of ent-Ancistrocladinium A

Kyung Hee Kim, Cheol Hong Cheon

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

10 Citations (Scopus)

Abstract

An asymmetric total synthesis of ent-ancistrocladinium A was developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl-2-propanone and naphthylamine followed by a Bischler–Napieralski reaction. Direct use of the naphthyl moiety in the amine as a key building block in the natural product allowed us to achieve the total synthesis of ancistrocladinium A in only three steps from the known starting materials. (Figure presented.).

Original language	English
Pages (from-to)	2883-2888
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	358
Issue number	18
DOIs	https://doi.org/10.1002/adsc.201600472
Publication status	Published - 2016 Sept 15

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

ancistrocladinium A
chiral phosphoric acid catalysis
naphthylisoquinoline alkaloids
reductive amination
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201600472

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title = "Concise Asymmetric Total Synthesis of ent-Ancistrocladinium A",

abstract = "An asymmetric total synthesis of ent-ancistrocladinium A was developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl-2-propanone and naphthylamine followed by a Bischler–Napieralski reaction. Direct use of the naphthyl moiety in the amine as a key building block in the natural product allowed us to achieve the total synthesis of ancistrocladinium A in only three steps from the known starting materials. (Figure presented.).",

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AU - Cheon, Cheol Hong

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N2 - An asymmetric total synthesis of ent-ancistrocladinium A was developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl-2-propanone and naphthylamine followed by a Bischler–Napieralski reaction. Direct use of the naphthyl moiety in the amine as a key building block in the natural product allowed us to achieve the total synthesis of ancistrocladinium A in only three steps from the known starting materials. (Figure presented.).

AB - An asymmetric total synthesis of ent-ancistrocladinium A was developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl-2-propanone and naphthylamine followed by a Bischler–Napieralski reaction. Direct use of the naphthyl moiety in the amine as a key building block in the natural product allowed us to achieve the total synthesis of ancistrocladinium A in only three steps from the known starting materials. (Figure presented.).

KW - ancistrocladinium A

KW - chiral phosphoric acid catalysis

KW - naphthylisoquinoline alkaloids

KW - reductive amination

KW - total synthesis

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JF - Advanced Synthesis and Catalysis

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ER -

Concise Asymmetric Total Synthesis of ent-Ancistrocladinium A

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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