A new asymmetric synthesis of (R)-3-methylpyrrolidine alkaloids starting from (S)-malic acid

Xiao Zheng; Pei Qiang Huang; Yuan Ping Ruan; Albert W.M. Lee; Wing Hong Chan

doi:10.3987/com-01-9266

A new asymmetric synthesis of (R)-3-methylpyrrolidine alkaloids starting from (S)-malic acid

Xiao Zheng
, Pei Qiang Huang^*
, Yuan Ping Ruan
, Albert W.M. Lee
, Wing Hong Chan

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

4 Citations (Scopus)

Abstract

Diastereoselective methylation of dimethyl (S)-malate (8) followed by two three-step reductive dehydroxylation procedures afforded dimethyl (R)-2-methylsuccinate (16) in 80.2% and 84.7% ee respectively, the later was further transformed into the natural enantiomers of ant venom alkaloids (R)-leptothoracine (1) and (R)-3-methyl-N-(2-phenylethyl)pyrrolidine (2) and (3R, 2'S)-3-methyl-N-(2-methylbutyl)pyrrolidine (3).

Original language	English
Pages (from-to)	1505-1518
Number of pages	14
Journal	Heterocycles
Volume	55
Issue number	8
DOIs	https://doi.org/10.3987/com-01-9266
Publication status	Published - 1 Aug 2001

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@article{0ea653c8a82c4bd78edd549cc9a5fc78,

title = "A new asymmetric synthesis of (R)-3-methylpyrrolidine alkaloids starting from (S)-malic acid",

abstract = "Diastereoselective methylation of dimethyl (S)-malate (8) followed by two three-step reductive dehydroxylation procedures afforded dimethyl (R)-2-methylsuccinate (16) in 80.2\% and 84.7\% ee respectively, the later was further transformed into the natural enantiomers of ant venom alkaloids (R)-leptothoracine (1) and (R)-3-methyl-N-(2-phenylethyl)pyrrolidine (2) and (3R, 2'S)-3-methyl-N-(2-methylbutyl)pyrrolidine (3).",

author = "Xiao Zheng and Huang, \{Pei Qiang\} and Ruan, \{Yuan Ping\} and Lee, \{Albert W.M.\} and Chan, \{Wing Hong\}",

year = "2001",

month = aug,

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doi = "10.3987/com-01-9266",

language = "English",

volume = "55",

pages = "1505--1518",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

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}

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T1 - A new asymmetric synthesis of (R)-3-methylpyrrolidine alkaloids starting from (S)-malic acid

AU - Zheng, Xiao

AU - Huang, Pei Qiang

AU - Ruan, Yuan Ping

AU - Lee, Albert W.M.

AU - Chan, Wing Hong

PY - 2001/8/1

Y1 - 2001/8/1

N2 - Diastereoselective methylation of dimethyl (S)-malate (8) followed by two three-step reductive dehydroxylation procedures afforded dimethyl (R)-2-methylsuccinate (16) in 80.2% and 84.7% ee respectively, the later was further transformed into the natural enantiomers of ant venom alkaloids (R)-leptothoracine (1) and (R)-3-methyl-N-(2-phenylethyl)pyrrolidine (2) and (3R, 2'S)-3-methyl-N-(2-methylbutyl)pyrrolidine (3).

AB - Diastereoselective methylation of dimethyl (S)-malate (8) followed by two three-step reductive dehydroxylation procedures afforded dimethyl (R)-2-methylsuccinate (16) in 80.2% and 84.7% ee respectively, the later was further transformed into the natural enantiomers of ant venom alkaloids (R)-leptothoracine (1) and (R)-3-methyl-N-(2-phenylethyl)pyrrolidine (2) and (3R, 2'S)-3-methyl-N-(2-methylbutyl)pyrrolidine (3).

UR - https://www.scopus.com/pages/publications/0041874946

U2 - 10.3987/com-01-9266

DO - 10.3987/com-01-9266

M3 - Journal article

AN - SCOPUS:0041874946

SN - 0385-5414

VL - 55

SP - 1505

EP - 1518

JO - Heterocycles

JF - Heterocycles

IS - 8

ER -

A new asymmetric synthesis of (R)-3-methylpyrrolidine alkaloids starting from (S)-malic acid

Abstract

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