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Total Synthesis and Structural Revision of Mangrolide D


Hattori, Hiromu; Hoff, Lukas V; Gademann, Karl (2019). Total Synthesis and Structural Revision of Mangrolide D. Organic Letters, 21(9):3456-3459.

Abstract

The unique 18-membered macrocyclic natural product mangrolide D was prepared in totally synthetic form. Key steps feature an Au-catalyzed glycosylation, aza-Michael addition, and LaLi3tris(binaphthoxide) catalyzed epoxidation. Detailed analysis of the constitution and configuration of the carbohydrate segment and the total synthesis of the revised structure led to structural revision of the originally proposed structure.

Abstract

The unique 18-membered macrocyclic natural product mangrolide D was prepared in totally synthetic form. Key steps feature an Au-catalyzed glycosylation, aza-Michael addition, and LaLi3tris(binaphthoxide) catalyzed epoxidation. Detailed analysis of the constitution and configuration of the carbohydrate segment and the total synthesis of the revised structure led to structural revision of the originally proposed structure.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Life Sciences > Biochemistry
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:Physical and Theoretical Chemistry, Organic Chemistry, Biochemistry
Language:English
Date:3 May 2019
Deposited On:31 Oct 2019 14:17
Last Modified:29 Jul 2020 11:36
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acs.orglett.9b01256
Project Information:
  • : FunderSNSF
  • : Grant ID200021_182043
  • : Project TitleMechanism-Based Design, Synthesis, Biological Evaluation, and Delivery of Next-Generation Antibiotics

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