Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins

Tomonori Mori; Yukiko Satouchi; Hiraku Tohmiya; Shuhei Higashibayashi; Kimiko Hashimoto; Masaya Nakata

doi:10.1016/j.tetlet.2005.07.121

Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins

Tomonori Mori, Yukiko Satouchi, Hiraku Tohmiya, Shuhei Higashibayashi, Kimiko Hashimoto, Masaya Nakata

薬科学科

研究成果: Article › 査読

13 被引用数 (Scopus)

抄録

Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins, members of the thiostrepton family of peptide antibiotics, has been achieved featuring the one-pot olefination via the Matsumura- Boekelheide rearrangement "using trifluoromethanesulfonic anhydride and triethylamine" and the stereoselective addition reaction controlled by the stereocenter of the peri-position.

本文言語	English
ページ（範囲）	6417-6422
ページ数	6
ジャーナル	Tetrahedron Letters
巻	46
号	38
DOI	https://doi.org/10.1016/j.tetlet.2005.07.121
出版ステータス	Published - 2005 9月 19

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/j.tetlet.2005.07.121

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引用スタイル

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title = "Synthetic studies on thiostrepton family of peptide antibiotics: Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins",

abstract = "Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins, members of the thiostrepton family of peptide antibiotics, has been achieved featuring the one-pot olefination via the Matsumura- Boekelheide rearrangement {"}using trifluoromethanesulfonic anhydride and triethylamine{"} and the stereoselective addition reaction controlled by the stereocenter of the peri-position.",

keywords = "Dihydroquinoline, Matsumura-Boekelheide rearrangement, Siomycins, Stereoselective addition, Thiostrepton",

author = "Tomonori Mori and Yukiko Satouchi and Hiraku Tohmiya and Shuhei Higashibayashi and Kimiko Hashimoto and Masaya Nakata",

note = "Funding Information: We thank Drs. Takashiro Akitsu and Masaru Yao (Keio University) for X-ray crystallographic analysis. This research was partially supported by a Grant-in-Aid for the 21st Century COE program {\textquoteleft}KEIO Life Conjugate Chemistry{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan and a Grant-in-Aid for Scientific Research on Priority Areas (A) {\textquoteleft}Exploitation of Multi-Element Cyclic Molecules{\textquoteright} from the Ministry of Education, Culture, Sports, Science and Technology, Japan.",

year = "2005",

month = sep,

day = "19",

doi = "10.1016/j.tetlet.2005.07.121",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Synthetic studies on thiostrepton family of peptide antibiotics

T2 - Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins

AU - Mori, Tomonori

AU - Satouchi, Yukiko

AU - Tohmiya, Hiraku

AU - Higashibayashi, Shuhei

AU - Hashimoto, Kimiko

AU - Nakata, Masaya

N1 - Funding Information: We thank Drs. Takashiro Akitsu and Masaru Yao (Keio University) for X-ray crystallographic analysis. This research was partially supported by a Grant-in-Aid for the 21st Century COE program ‘KEIO Life Conjugate Chemistry’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan and a Grant-in-Aid for Scientific Research on Priority Areas (A) ‘Exploitation of Multi-Element Cyclic Molecules’ from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2005/9/19

Y1 - 2005/9/19

N2 - Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins, members of the thiostrepton family of peptide antibiotics, has been achieved featuring the one-pot olefination via the Matsumura- Boekelheide rearrangement "using trifluoromethanesulfonic anhydride and triethylamine" and the stereoselective addition reaction controlled by the stereocenter of the peri-position.

AB - Synthesis of the dihydroquinoline portion of thiostrepton, the siomycins, and the thiopeptins, members of the thiostrepton family of peptide antibiotics, has been achieved featuring the one-pot olefination via the Matsumura- Boekelheide rearrangement "using trifluoromethanesulfonic anhydride and triethylamine" and the stereoselective addition reaction controlled by the stereocenter of the peri-position.

KW - Dihydroquinoline

KW - Matsumura-Boekelheide rearrangement

KW - Siomycins

KW - Stereoselective addition

KW - Thiostrepton

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