Total synthesis of siomycin A: Completion of the total synthesis

Tomonori Mori; Shuhei Higashibayashi; Taiji Goto; Mitsunori O. Kohno; Yukiko Satouchi; Kazuyuki Shinko; Kengo Suzuki; Shunya Suzuki; Hiraku Tohmiya; Kimiko Hashimoto; Masaya Nakata

doi:10.1002/asia.200800033

Total synthesis of siomycin A: Completion of the total synthesis

Tomonori Mori, Shuhei Higashibayashi, Taiji Goto, Mitsunori O. Kohno, Yukiko Satouchi, Kazuyuki Shinko, Kengo Suzuki, Shunya Suzuki, Hiraku Tohmiya, Kimiko Hashimoto, Masaya Nakata

School of Pharmaceutical Sciences

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

15 Citations (Scopus)

Abstract

The total synthesis of siomycin A (1), a representative compound of the thiostrepton family of peptide antibiotics, was achieved by incorporating the five synthetic segments A (2), B (3), C (4), D (5), and E (6). The dehydropiperidine segment A (2) was esterified with the dihydroquinoline segment C (4), and the subsequent coupling with the β-phenylselenoalanine dipeptide segment D (5) at the segment C portion followed by lactamization between the segments A and D gave segment A-C-D (27). This was amidated with the pentapeptide segment B( 3) at the segment A portion followed by one-pot cyclization (between segments A and B) and elongation (with the β-phenylselenoalanine dipeptide segment E (6) at the segment A portion), thus furnishing siomycin A (1).

Original language	English
Pages (from-to)	1013-1025
Number of pages	13
Journal	Chemistry - An Asian Journal
Volume	3
Issue number	6
DOIs	https://doi.org/10.1002/asia.200800033
Publication status	Published - 2008 Jun 2

Keywords

Cyclization
Epoxides
Natural products
Siomycin A
Total synthesis

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.1002/asia.200800033

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title = "Total synthesis of siomycin A: Completion of the total synthesis",

abstract = "The total synthesis of siomycin A (1), a representative compound of the thiostrepton family of peptide antibiotics, was achieved by incorporating the five synthetic segments A (2), B (3), C (4), D (5), and E (6). The dehydropiperidine segment A (2) was esterified with the dihydroquinoline segment C (4), and the subsequent coupling with the β-phenylselenoalanine dipeptide segment D (5) at the segment C portion followed by lactamization between the segments A and D gave segment A-C-D (27). This was amidated with the pentapeptide segment B( 3) at the segment A portion followed by one-pot cyclization (between segments A and B) and elongation (with the β-phenylselenoalanine dipeptide segment E (6) at the segment A portion), thus furnishing siomycin A (1).",

keywords = "Cyclization, Epoxides, Natural products, Siomycin A, Total synthesis",

author = "Tomonori Mori and Shuhei Higashibayashi and Taiji Goto and Kohno, {Mitsunori O.} and Yukiko Satouchi and Kazuyuki Shinko and Kengo Suzuki and Shunya Suzuki and Hiraku Tohmiya and Kimiko Hashimoto and Masaya Nakata",

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month = jun,

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doi = "10.1002/asia.200800033",

language = "English",

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AU - Mori, Tomonori

AU - Higashibayashi, Shuhei

AU - Goto, Taiji

AU - Kohno, Mitsunori O.

AU - Satouchi, Yukiko

AU - Shinko, Kazuyuki

AU - Suzuki, Kengo

AU - Suzuki, Shunya

AU - Tohmiya, Hiraku

AU - Hashimoto, Kimiko

AU - Nakata, Masaya

PY - 2008/6/2

Y1 - 2008/6/2

N2 - The total synthesis of siomycin A (1), a representative compound of the thiostrepton family of peptide antibiotics, was achieved by incorporating the five synthetic segments A (2), B (3), C (4), D (5), and E (6). The dehydropiperidine segment A (2) was esterified with the dihydroquinoline segment C (4), and the subsequent coupling with the β-phenylselenoalanine dipeptide segment D (5) at the segment C portion followed by lactamization between the segments A and D gave segment A-C-D (27). This was amidated with the pentapeptide segment B( 3) at the segment A portion followed by one-pot cyclization (between segments A and B) and elongation (with the β-phenylselenoalanine dipeptide segment E (6) at the segment A portion), thus furnishing siomycin A (1).

AB - The total synthesis of siomycin A (1), a representative compound of the thiostrepton family of peptide antibiotics, was achieved by incorporating the five synthetic segments A (2), B (3), C (4), D (5), and E (6). The dehydropiperidine segment A (2) was esterified with the dihydroquinoline segment C (4), and the subsequent coupling with the β-phenylselenoalanine dipeptide segment D (5) at the segment C portion followed by lactamization between the segments A and D gave segment A-C-D (27). This was amidated with the pentapeptide segment B( 3) at the segment A portion followed by one-pot cyclization (between segments A and B) and elongation (with the β-phenylselenoalanine dipeptide segment E (6) at the segment A portion), thus furnishing siomycin A (1).

KW - Cyclization

KW - Epoxides

KW - Natural products

KW - Siomycin A

KW - Total synthesis

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JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

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ER -

Total synthesis of siomycin A: Completion of the total synthesis

Abstract

Keywords

ASJC Scopus subject areas

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