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

X. Zheng; P. Q. Huang; Y. P. Ruan; A. Lee; W. Hong Chan

doi:10.1080/1057563029001/4854

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

X. Zheng
, P. Q. Huang^*
, Y. P. Ruan
, A. Lee
, W. Hong Chan

^*Corresponding author for this work

Department of Chemistry

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

6 Citations (Scopus)

Abstract

Diastereoselective methylation of dimethyl (S)-malate 7, followed by two, three-step reductive de-hydroxylation procedures afforded dimethyl (R)-2-methylsuccinate 11 in 80.2% e.e. and 84.7% e.e., respectively. The latter compound was further transformed into the natural enantiomers of the ant venom alkaloids (R)-leptothoracine 1 and (R)-3-methyl-N-(2-phenylethyl)-pyrrolidine 2.

Original language	English
Pages (from-to)	53-56
Number of pages	4
Journal	Natural Product Letters
Volume	16
Issue number	1
DOIs	https://doi.org/10.1080/1057563029001/4854
Publication status	Published - 2002

User-Defined Keywords

Alkaloids
Asymmetric synthesis
Malic acid
Pyrrolidines

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10.1080/1057563029001/4854

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@article{69dd66358a494774a87dfd1070b2899c,

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

abstract = "Diastereoselective methylation of dimethyl (S)-malate 7, followed by two, three-step reductive de-hydroxylation procedures afforded dimethyl (R)-2-methylsuccinate 11 in 80.2\% e.e. and 84.7\% e.e., respectively. The latter compound was further transformed into the natural enantiomers of the ant venom alkaloids (R)-leptothoracine 1 and (R)-3-methyl-N-(2-phenylethyl)-pyrrolidine 2.",

keywords = "Alkaloids, Asymmetric synthesis, Malic acid, Pyrrolidines",

author = "X. Zheng and Huang, \{P. Q.\} and Ruan, \{Y. P.\} and A. Lee and \{Hong Chan\}, W.",

note = "Funding Information: This work is supported by the National Science Fund for Distinguished Young Investigators (29625204) and the NSF of China (29832020), the Foundation for University Key Teacher by the Ministry of Education and Xiamen University. Pei-Qiang Huang dedicates this paper to the memory of his father.",

year = "2002",

doi = "10.1080/1057563029001/4854",

language = "English",

volume = "16",

pages = "53--56",

journal = "Natural Product Letters",

issn = "1057-5634",

publisher = "Taylor and Francis Ltd.",

number = "1",

}

TY - JOUR

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

AU - Zheng, X.

AU - Huang, P. Q.

AU - Ruan, Y. P.

AU - Lee, A.

AU - Hong Chan, W.

N1 - Funding Information: This work is supported by the National Science Fund for Distinguished Young Investigators (29625204) and the NSF of China (29832020), the Foundation for University Key Teacher by the Ministry of Education and Xiamen University. Pei-Qiang Huang dedicates this paper to the memory of his father.

PY - 2002

Y1 - 2002

N2 - Diastereoselective methylation of dimethyl (S)-malate 7, followed by two, three-step reductive de-hydroxylation procedures afforded dimethyl (R)-2-methylsuccinate 11 in 80.2% e.e. and 84.7% e.e., respectively. The latter compound was further transformed into the natural enantiomers of the ant venom alkaloids (R)-leptothoracine 1 and (R)-3-methyl-N-(2-phenylethyl)-pyrrolidine 2.

AB - Diastereoselective methylation of dimethyl (S)-malate 7, followed by two, three-step reductive de-hydroxylation procedures afforded dimethyl (R)-2-methylsuccinate 11 in 80.2% e.e. and 84.7% e.e., respectively. The latter compound was further transformed into the natural enantiomers of the ant venom alkaloids (R)-leptothoracine 1 and (R)-3-methyl-N-(2-phenylethyl)-pyrrolidine 2.

KW - Alkaloids

KW - Asymmetric synthesis

KW - Malic acid

KW - Pyrrolidines

UR - https://www.scopus.com/pages/publications/0036105796

U2 - 10.1080/1057563029001/4854

DO - 10.1080/1057563029001/4854

M3 - Journal article

C2 - 11942683

AN - SCOPUS:0036105796

SN - 1057-5634

VL - 16

SP - 53

EP - 56

JO - Natural Product Letters

JF - Natural Product Letters

IS - 1

ER -

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

Abstract

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