Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction

Ryotaro Okawa; Courtney C. Aldrich; Satoshi Ichikawa

doi:10.1039/d2cc02442j

Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction

Ryotaro Okawa, Courtney C. Aldrich, Satoshi Ichikawa

Medicinal Chemistry

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

2 Scopus citations

Abstract

A total synthesis of pseudouridimycin (1) was accomplished featuring an unusual oxime Ugi-type multicomponent condensation to simultaneously construct the dipeptide moiety of this peptidyl nucleoside antibiotic. In this synthetic route 1 is readily accessible via a longest linear sequence of 9 synthetic steps from pseudouridine. This strategy can be applicable to a variety of pseudouridimycin analogues.

Original language	English (US)
Pages (from-to)	7956-7959
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	57
DOIs	https://doi.org/10.1039/d2cc02442j
State	Published - Jun 17 2022

Bibliographical note

Publisher Copyright:
© 2022 The Royal Society of Chemistry.

PubMed: MeSH publication types

Journal Article

Access

10.1039/d2cc02442j

OpenUrl availability

Full text

Cite this

@article{027edddc39bd474ca133780858800678,

title = "Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction",

abstract = "A total synthesis of pseudouridimycin (1) was accomplished featuring an unusual oxime Ugi-type multicomponent condensation to simultaneously construct the dipeptide moiety of this peptidyl nucleoside antibiotic. In this synthetic route 1 is readily accessible via a longest linear sequence of 9 synthetic steps from pseudouridine. This strategy can be applicable to a variety of pseudouridimycin analogues.",

author = "Ryotaro Okawa and Aldrich, {Courtney C.} and Satoshi Ichikawa",

note = "Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

month = jun,

day = "17",

doi = "10.1039/d2cc02442j",

language = "English (US)",

volume = "58",

pages = "7956--7959",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "57",

}

TY - JOUR

T1 - Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction

AU - Okawa, Ryotaro

AU - Aldrich, Courtney C.

AU - Ichikawa, Satoshi

PY - 2022/6/17

Y1 - 2022/6/17

N2 - A total synthesis of pseudouridimycin (1) was accomplished featuring an unusual oxime Ugi-type multicomponent condensation to simultaneously construct the dipeptide moiety of this peptidyl nucleoside antibiotic. In this synthetic route 1 is readily accessible via a longest linear sequence of 9 synthetic steps from pseudouridine. This strategy can be applicable to a variety of pseudouridimycin analogues.

AB - A total synthesis of pseudouridimycin (1) was accomplished featuring an unusual oxime Ugi-type multicomponent condensation to simultaneously construct the dipeptide moiety of this peptidyl nucleoside antibiotic. In this synthetic route 1 is readily accessible via a longest linear sequence of 9 synthetic steps from pseudouridine. This strategy can be applicable to a variety of pseudouridimycin analogues.

UR - http://www.scopus.com/inward/record.url?scp=85133136009&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85133136009&partnerID=8YFLogxK

U2 - 10.1039/d2cc02442j

DO - 10.1039/d2cc02442j

M3 - Article

C2 - 35757838

AN - SCOPUS:85133136009

SN - 1359-7345

VL - 58

SP - 7956

EP - 7959

JO - Chemical Communications

JF - Chemical Communications

IS - 57

ER -

Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction

Abstract

Bibliographical note

PubMed: MeSH publication types

Access

OpenUrl availability

Other files and links

Fingerprint

Cite this