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Convergent synthesis and structural confirmation of phellodonin and sarcodonin ?.

ABSTRACT: The first synthesis of members of the sarcodonin family, phellodonin and sarcodonin ?, is reported herein. This verifies that the unprecedented and seemingly unstable N,N-dioxide-containing benzodioxazine framework can be constructed in the laboratory and lends further support to the proposed structures. The key step in the synthesis involves a biomimetic hetero-Diels-Alder reaction between a pyrazine N-oxide and an ortho-quinone.

SUBMITTER: Usui I

PROVIDER: S-EPMC3653569 | biostudies-literature | 2013 May

REPOSITORIES: biostudies-literature

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Convergent synthesis and structural confirmation of phellodonin and sarcodonin ε.

Usui Ippei I Lin David W DW Masuda Takeshi T Baran Phil S PS

Organic letters 20130411 9

The first synthesis of members of the sarcodonin family, phellodonin and sarcodonin ε, is reported herein. This verifies that the unprecedented and seemingly unstable N,N-dioxide-containing benzodioxazine framework can be constructed in the laboratory and lends further support to the proposed structures. The key step in the synthesis involves a biomimetic hetero-Diels-Alder reaction between a pyrazine N-oxide and an ortho-quinone. ...[more]

PMID: 23577748

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