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Synthesis of the C50 diastereomers of the C33–C51 fragment of stambomycin D

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Wang, Yongchen, Chintalapudi, Venkaiah, Gudmundsson, Haraldur G., Challis, Gregory L. and Anderson, Edward A. (2021) Synthesis of the C50 diastereomers of the C33–C51 fragment of stambomycin D. Organic Chemistry Frontiers, 9 (2). pp. 445-449. doi:10.1039/d1qo01635k ISSN 2052-4129.

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Official URL: https://doi.org/10.1039/d1qo01635k

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Abstract

As products of genome mining, the stereochemical assignment of the macrolide antibiotics stambomycins A–D has been made on the basis of sequence analysis of the associated polyketide synthase, aside from two stereocentres at C28 and C50. Here we describe syntheses of the two C50 diastereomers of the C33–C51 region of the stambomycins, which support the PKS-based configurational assignment, and establish a strategy suitable for access to the extended stambomycin framework.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Q Science > QP Physiology
R Medicine > RM Therapeutics. Pharmacology
Divisions: Faculty of Science, Engineering and Medicine > Science > Chemistry
SWORD Depositor: Library Publications Router
Library of Congress Subject Headings (LCSH): Macrolide antibiotics, Stereochemistry, Polyketides -- Synthesis, Diastereoisomers
Journal or Publication Title: Organic Chemistry Frontiers
Publisher: Royal Society of Chemistry
ISSN: 2052-4129
Official Date: 8 December 2021
Dates:
DateEvent
8 December 2021Published
8 December 2021Accepted
Volume: 9
Number: 2
Page Range: pp. 445-449
DOI: 10.1039/d1qo01635k
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access
Date of first compliant deposit: 7 March 2022
Date of first compliant Open Access: 8 December 2022
RIOXX Funder/Project Grant:
Project/Grant IDRIOXX Funder NameFunder ID
702385H2020 Marie Skłodowska-Curie Actionshttp://dx.doi.org/10.13039/100010665
RPG-2015-003Leverhulme Trusthttp://dx.doi.org/10.13039/501100000275
EP/S013172/1[EPSRC] Engineering and Physical Sciences Research Councilhttp://dx.doi.org/10.13039/501100000266

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