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Exploring endoperoxides as a new entry for the synthesis of branched azasugars.

ABSTRACT: A new class of nitrogen-containing endoperoxides were synthesised by a photochemical [4 + 2]-cycloaddition between a diene and singlet oxygen. The endoperoxides were dihydroxylated and protected to provide a series of endoperoxide building blocks for organic synthesis, with potential use as precursors for the synthesis of branched azasugars. Preliminary exploration of the chemistry of these building blocks provided access to a variety of derivatives including tetrahydrofurans, epoxides and protected amino-tetraols.

SUBMITTER: Domeyer S

PROVIDER: S-EPMC5389192 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

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Exploring endoperoxides as a new entry for the synthesis of branched azasugars.

Domeyer Svenja S Bjerregaard Mark M Johansson Henrik H Sejer Pedersen Daniel D

Beilstein journal of organic chemistry 20170403

A new class of nitrogen-containing endoperoxides were synthesised by a photochemical [4 + 2]-cycloaddition between a diene and singlet oxygen. The endoperoxides were dihydroxylated and protected to provide a series of endoperoxide building blocks for organic synthesis, with potential use as precursors for the synthesis of branched azasugars. Preliminary exploration of the chemistry of these building blocks provided access to a variety of derivatives including tetrahydrofurans, epoxides and prote ...[more]

PMID: 28487758

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