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

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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

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© 2022 The Royal Society of Chemistry.

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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",

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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.

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

Abstract

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