Syntheses and odor descriptions of cyclopropanated compounds part 5. Analogs of methyl jasmonate to fix the relative configuration of the two side chains

Hiromasa Kiyota; Shin Ya Takigawa; Shigefumi Kuwahara

doi:10.1002/hlca.200490164

Syntheses and odor descriptions of cyclopropanated compounds part 5. Analogs of methyl jasmonate to fix the relative configuration of the two side chains

Hiromasa Kiyota, Shin Ya Takigawa, Shigefumi Kuwahara

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

10 Citations (Scopus)

Abstract

Analogs of methyl jasmonate (=methyl (1R*,2R*)-3-oxo-2-[(Z)- pent-2-enyl]cyclopentaneacetate; MJA) bearing a cyclopropane ring, double bond, or a F-substituent were synthesized, and their odor characteristics were examined. Most of the analogs with the same stereochemical properties as methyl epijasmonate showed odor properties superior to MJA. Interestingly, the enol acetate of MJA had a diffusive orchid-like note.

Original language	English
Pages (from-to)	1854-1859
Number of pages	6
Journal	Helvetica Chimica Acta
Volume	87
Issue number	7
DOIs	https://doi.org/10.1002/hlca.200490164
Publication status	Published - Aug 24 2004
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

Access to Document

10.1002/hlca.200490164

Cite this

@article{e8e1c072779943688491917194a34850,

title = "Syntheses and odor descriptions of cyclopropanated compounds part 5. Analogs of methyl jasmonate to fix the relative configuration of the two side chains",

abstract = "Analogs of methyl jasmonate (=methyl (1R*,2R*)-3-oxo-2-[(Z)- pent-2-enyl]cyclopentaneacetate; MJA) bearing a cyclopropane ring, double bond, or a F-substituent were synthesized, and their odor characteristics were examined. Most of the analogs with the same stereochemical properties as methyl epijasmonate showed odor properties superior to MJA. Interestingly, the enol acetate of MJA had a diffusive orchid-like note.",

author = "Hiromasa Kiyota and Takigawa, {Shin Ya} and Shigefumi Kuwahara",

year = "2004",

month = aug,

day = "24",

doi = "10.1002/hlca.200490164",

language = "English",

volume = "87",

pages = "1854--1859",

journal = "Helvetica Chimica Acta",

issn = "0018-019X",

publisher = "Verlag Helvetica Chimica Acta AG",

number = "7",

}

TY - JOUR

T1 - Syntheses and odor descriptions of cyclopropanated compounds part 5. Analogs of methyl jasmonate to fix the relative configuration of the two side chains

AU - Kiyota, Hiromasa

AU - Takigawa, Shin Ya

AU - Kuwahara, Shigefumi

PY - 2004/8/24

Y1 - 2004/8/24

N2 - Analogs of methyl jasmonate (=methyl (1R*,2R*)-3-oxo-2-[(Z)- pent-2-enyl]cyclopentaneacetate; MJA) bearing a cyclopropane ring, double bond, or a F-substituent were synthesized, and their odor characteristics were examined. Most of the analogs with the same stereochemical properties as methyl epijasmonate showed odor properties superior to MJA. Interestingly, the enol acetate of MJA had a diffusive orchid-like note.

AB - Analogs of methyl jasmonate (=methyl (1R*,2R*)-3-oxo-2-[(Z)- pent-2-enyl]cyclopentaneacetate; MJA) bearing a cyclopropane ring, double bond, or a F-substituent were synthesized, and their odor characteristics were examined. Most of the analogs with the same stereochemical properties as methyl epijasmonate showed odor properties superior to MJA. Interestingly, the enol acetate of MJA had a diffusive orchid-like note.

UR - http://www.scopus.com/inward/record.url?scp=4043096159&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=4043096159&partnerID=8YFLogxK

U2 - 10.1002/hlca.200490164

DO - 10.1002/hlca.200490164

M3 - Article

AN - SCOPUS:4043096159

SN - 0018-019X

VL - 87

SP - 1854

EP - 1859

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 7

ER -

Syntheses and odor descriptions of cyclopropanated compounds part 5. Analogs of methyl jasmonate to fix the relative configuration of the two side chains

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this