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Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone


Schnell, Simon D; Linden, Anthony; Gademann, Karl (2019). Synthesis of Two Key Fragments of the Complex Polyhalogenated Marine Meroterpenoid Azamerone. Organic Letters, 21(4):1144-1147.

Abstract

A concise route toward two advanced fragments in the context of the total synthesis of the unique natural product azamerone is reported. Key synthetic features include the enantioselective synthesis of an epoxysilane and its Lewis-acid-induced cyclization and the installation of the pyridazine ring via a formylation/condensation sequence. This route provides strategic insights into the chemistry of phthalazinediols, facilitating synthetic approaches toward this class of natural products.

Abstract

A concise route toward two advanced fragments in the context of the total synthesis of the unique natural product azamerone is reported. Key synthetic features include the enantioselective synthesis of an epoxysilane and its Lewis-acid-induced cyclization and the installation of the pyridazine ring via a formylation/condensation sequence. This route provides strategic insights into the chemistry of phthalazinediols, facilitating synthetic approaches toward this class of natural products.

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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:15 February 2019
Deposited On:31 Oct 2019 14:29
Last Modified:23 Apr 2021 07:05
Publisher:American Chemical Society (ACS)
ISSN:1523-7052
OA Status:Green
Publisher DOI:https://doi.org/10.1021/acs.orglett.9b00090

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