Synthesis and odor properties of Phantolide analogues

Masashi Kawasaki; Saki Kuroyanagi; Takuya Ito; Hiroyuki Morita; Yasuo Tanaka; Naoki Toyooka

doi:10.1016/j.tet.2017.02.055

Synthesis and odor properties of Phantolide analogues

Masashi Kawasaki, Saki Kuroyanagi, Takuya Ito, Hiroyuki Morita, Yasuo Tanaka, Naoki Toyooka^*

^*Corresponding author for this work

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

5 Scopus citations

Abstract

Phantolide analogues 1a–1d were newly synthesized to evaluate their odor profiles. The enantiomers of 1a and 1b were also synthesized. Both (S) enantiomers of 1a and 1b had musk odor although weakly, and but neither of the (R) enantiomers 1a and 1b had musk odor. During the investigations, we encountered the undesirable racemization in Friedel-Crafts reaction of the intermediate (S)-5.

Original language	English
Pages (from-to)	2089-2099
Number of pages	11
Journal	Tetrahedron
Volume	73
Issue number	15
DOIs	https://doi.org/10.1016/j.tet.2017.02.055
State	Published - 2017

Keywords

Asymmetric synthesis
Friedel-Crafts reaction
Lipase
Phantolide
Racemization

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2017.02.055

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@article{e9239526a3e2418e9b9993905d31876c,

title = "Synthesis and odor properties of Phantolide analogues",

abstract = "Phantolide analogues 1a–1d were newly synthesized to evaluate their odor profiles. The enantiomers of 1a and 1b were also synthesized. Both (S) enantiomers of 1a and 1b had musk odor although weakly, and but neither of the (R) enantiomers 1a and 1b had musk odor. During the investigations, we encountered the undesirable racemization in Friedel-Crafts reaction of the intermediate (S)-5.",

keywords = "Asymmetric synthesis, Friedel-Crafts reaction, Lipase, Phantolide, Racemization",

author = "Masashi Kawasaki and Saki Kuroyanagi and Takuya Ito and Hiroyuki Morita and Yasuo Tanaka and Naoki Toyooka",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2017",

doi = "10.1016/j.tet.2017.02.055",

language = "英語",

volume = "73",

pages = "2089--2099",

journal = "Tetrahedron",

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TY - JOUR

T1 - Synthesis and odor properties of Phantolide analogues

AU - Kawasaki, Masashi

AU - Kuroyanagi, Saki

AU - Ito, Takuya

AU - Morita, Hiroyuki

AU - Tanaka, Yasuo

AU - Toyooka, Naoki

PY - 2017

Y1 - 2017

N2 - Phantolide analogues 1a–1d were newly synthesized to evaluate their odor profiles. The enantiomers of 1a and 1b were also synthesized. Both (S) enantiomers of 1a and 1b had musk odor although weakly, and but neither of the (R) enantiomers 1a and 1b had musk odor. During the investigations, we encountered the undesirable racemization in Friedel-Crafts reaction of the intermediate (S)-5.

AB - Phantolide analogues 1a–1d were newly synthesized to evaluate their odor profiles. The enantiomers of 1a and 1b were also synthesized. Both (S) enantiomers of 1a and 1b had musk odor although weakly, and but neither of the (R) enantiomers 1a and 1b had musk odor. During the investigations, we encountered the undesirable racemization in Friedel-Crafts reaction of the intermediate (S)-5.

KW - Asymmetric synthesis

KW - Friedel-Crafts reaction

KW - Lipase

KW - Phantolide

KW - Racemization

UR - http://www.scopus.com/inward/record.url?scp=85014412034&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2017.02.055

DO - 10.1016/j.tet.2017.02.055

M3 - 学術論文

AN - SCOPUS:85014412034

SN - 0040-4020

VL - 73

SP - 2089

EP - 2099

JO - Tetrahedron

JF - Tetrahedron

IS - 15

ER -

Synthesis and odor properties of Phantolide analogues

Abstract

Keywords

ASJC Scopus subject areas

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