An Efficient Synthesis of Methyl dl-cis-Jasmonate

Francis Johnson; Kenneth G. Paul; D. Favara

doi:10.1021/jo00143a015

An Efficient Synthesis of Methyl dl-cis-Jasmonate

Francis Johnson
, Kenneth G. Paul
, D. Favara

Pharmacological Sciences

Dow Chemical
Gruppo Lepetit S.p.A.

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

21 Scopus citations

Abstract

An efficient synthesis of methyl dl-cis-jasmonate is described, starting from the previously described 2-(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]cyclopentanone (3), itself easily prepared from succinyl chloride and methyl potassium malonate. Alkylation of 3 with l-bromo-2-pentyne followed by selective removal of the 2-carbomethoxy group gave dehydrojasmonic acid. On esterification and reduction (H₂/Pd/C/pyridine) of the triple bond to the cis olefin, dehydrojasmonic acid afforded methyl dl-cis-jasmonate in 40% overall yield from succinyl chloride.

Original language	English
Pages (from-to)	4254-4255
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	47
Issue number	22
DOIs	https://doi.org/10.1021/jo00143a015
State	Published - 1982

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title = "An Efficient Synthesis of Methyl dl-cis-Jasmonate",

abstract = "An efficient synthesis of methyl dl-cis-jasmonate is described, starting from the previously described 2-(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]cyclopentanone (3), itself easily prepared from succinyl chloride and methyl potassium malonate. Alkylation of 3 with l-bromo-2-pentyne followed by selective removal of the 2-carbomethoxy group gave dehydrojasmonic acid. On esterification and reduction (H2/Pd/C/pyridine) of the triple bond to the cis olefin, dehydrojasmonic acid afforded methyl dl-cis-jasmonate in 40\% overall yield from succinyl chloride.",

author = "Francis Johnson and Paul, \{Kenneth G.\} and D. Favara",

year = "1982",

doi = "10.1021/jo00143a015",

language = "English",

volume = "47",

pages = "4254--4255",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

number = "22",

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T1 - An Efficient Synthesis of Methyl dl-cis-Jasmonate

AU - Johnson, Francis

AU - Paul, Kenneth G.

AU - Favara, D.

PY - 1982

Y1 - 1982

N2 - An efficient synthesis of methyl dl-cis-jasmonate is described, starting from the previously described 2-(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]cyclopentanone (3), itself easily prepared from succinyl chloride and methyl potassium malonate. Alkylation of 3 with l-bromo-2-pentyne followed by selective removal of the 2-carbomethoxy group gave dehydrojasmonic acid. On esterification and reduction (H2/Pd/C/pyridine) of the triple bond to the cis olefin, dehydrojasmonic acid afforded methyl dl-cis-jasmonate in 40% overall yield from succinyl chloride.

AB - An efficient synthesis of methyl dl-cis-jasmonate is described, starting from the previously described 2-(methoxycarbonyl)-3-[(methoxycarbonyl)methyl]cyclopentanone (3), itself easily prepared from succinyl chloride and methyl potassium malonate. Alkylation of 3 with l-bromo-2-pentyne followed by selective removal of the 2-carbomethoxy group gave dehydrojasmonic acid. On esterification and reduction (H2/Pd/C/pyridine) of the triple bond to the cis olefin, dehydrojasmonic acid afforded methyl dl-cis-jasmonate in 40% overall yield from succinyl chloride.

UR - https://www.scopus.com/pages/publications/0020452124

U2 - 10.1021/jo00143a015

DO - 10.1021/jo00143a015

M3 - Article

AN - SCOPUS:0020452124

SN - 0022-3263

VL - 47

SP - 4254

EP - 4255

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 22

ER -

An Efficient Synthesis of Methyl dl-cis-Jasmonate

Abstract

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