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

School of Pharmaceutical Sciences

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

13 Citations (Scopus)

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.

Original language	English
Pages (from-to)	6417-6422
Number of pages	6
Journal	Tetrahedron Letters
Volume	46
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2005.07.121
Publication status	Published - 2005 Sept 19

Keywords

Dihydroquinoline
Matsumura-Boekelheide rearrangement
Siomycins
Stereoselective addition
Thiostrepton

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2005.07.121

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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",

volume = "46",

pages = "6417--6422",

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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SN - 0040-4039

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JO - Tetrahedron Letters

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IS - 38

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

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