Asymmetric synthesis of (-)-lentiginosine by double aza-michael reaction

Sin Wei Liu; He Chu Hsu; Chiao Hsin Changa; Hui Hsu Gavin Tsai; Duen Ren Hou

doi:10.1002/ejoc.201000691

Asymmetric synthesis of (-)-lentiginosine by double aza-michael reaction

Sin Wei Liu, He Chu Hsu, Chiao Hsin Changa, Hui Hsu Gavin Tsai, Duen Ren Hou

Department of Chemistry

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

34 Scopus citations

Abstract

Total synthesis of (-)-lentiginosine (1) was achieved in nine steps from (3R,4R)-3,4-dihydroxy-l,5-hexadiene (2). Cross metathesis, vinyl addition and DDQ oxidation were applied to generate the key 3-oxonona-1,4,8-triene 6, which was cyclised to 4-oxopiperidine 7 by diastereoselective double aza-Michael reaction. Both theoretical and empirical studies support that the stereochemical assignment of the major Michael adduct is the desired (2R)-4-oxopiperidme 7.

Original language	English
Pages (from-to)	4771-4773
Number of pages	3
Journal	European Journal of Organic Chemistry
Issue number	25
DOIs	https://doi.org/10.1002/ejoc.201000691
State	Published - Sep 2010

Keywords

Alkaloids
Asymmetric synthesis
Aza-Michael reaction
Metathesis

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abstract = "Total synthesis of (-)-lentiginosine (1) was achieved in nine steps from (3R,4R)-3,4-dihydroxy-l,5-hexadiene (2). Cross metathesis, vinyl addition and DDQ oxidation were applied to generate the key 3-oxonona-1,4,8-triene 6, which was cyclised to 4-oxopiperidine 7 by diastereoselective double aza-Michael reaction. Both theoretical and empirical studies support that the stereochemical assignment of the major Michael adduct is the desired (2R)-4-oxopiperidme 7.",

keywords = "Alkaloids, Asymmetric synthesis, Aza-Michael reaction, Metathesis",

author = "Liu, {Sin Wei} and Hsu, {He Chu} and Changa, {Chiao Hsin} and Tsai, {Hui Hsu Gavin} and Hou, {Duen Ren}",

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T1 - Asymmetric synthesis of (-)-lentiginosine by double aza-michael reaction

AU - Liu, Sin Wei

AU - Hsu, He Chu

AU - Changa, Chiao Hsin

AU - Tsai, Hui Hsu Gavin

AU - Hou, Duen Ren

PY - 2010/9

Y1 - 2010/9

N2 - Total synthesis of (-)-lentiginosine (1) was achieved in nine steps from (3R,4R)-3,4-dihydroxy-l,5-hexadiene (2). Cross metathesis, vinyl addition and DDQ oxidation were applied to generate the key 3-oxonona-1,4,8-triene 6, which was cyclised to 4-oxopiperidine 7 by diastereoselective double aza-Michael reaction. Both theoretical and empirical studies support that the stereochemical assignment of the major Michael adduct is the desired (2R)-4-oxopiperidme 7.

AB - Total synthesis of (-)-lentiginosine (1) was achieved in nine steps from (3R,4R)-3,4-dihydroxy-l,5-hexadiene (2). Cross metathesis, vinyl addition and DDQ oxidation were applied to generate the key 3-oxonona-1,4,8-triene 6, which was cyclised to 4-oxopiperidine 7 by diastereoselective double aza-Michael reaction. Both theoretical and empirical studies support that the stereochemical assignment of the major Michael adduct is the desired (2R)-4-oxopiperidme 7.

KW - Alkaloids

KW - Asymmetric synthesis

KW - Aza-Michael reaction

KW - Metathesis

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DO - 10.1002/ejoc.201000691

M3 - 期刊論文

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SN - 1434-193X

SP - 4771

EP - 4773

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 25

ER -

Asymmetric synthesis of (-)-lentiginosine by double aza-michael reaction

Abstract

Keywords

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