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Ring strain and total syntheses of modified macrocycles of the isoplagiochin type.

ABSTRACT: Macrocycles of the bisbibenzyl-type are natural products that are found exclusively in bryophytes (liverworts). The molecular framework of the subtype "isoplagiochin" is of substantial structural interest because of the chirality of the entire molecule, which arises from two biaryl axes in combination with two helical two-carbon units in a cyclic arrangement. From a structural as well as a synthetic point of view we report on the total synthesis of compounds which possess more rigid two-carbon biaryl bridges like stilbene (E or Z) or even tolane moieties which were introduced starting with a Sonogashira protocol. The McMurry method proved to be a powerful tool for the cyclization to these considerably ring-strained macrocycles.

SUBMITTER: Speicher A

PROVIDER: S-EPMC2839535 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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Ring strain and total syntheses of modified macrocycles of the isoplagiochin type.

Speicher Andreas A Backes Timo T Hesidens Kerstin K Kolz Jürgen J

Beilstein journal of organic chemistry 20091201

Macrocycles of the bisbibenzyl-type are natural products that are found exclusively in bryophytes (liverworts). The molecular framework of the subtype "isoplagiochin" is of substantial structural interest because of the chirality of the entire molecule, which arises from two biaryl axes in combination with two helical two-carbon units in a cyclic arrangement. From a structural as well as a synthetic point of view we report on the total synthesis of compounds which possess more rigid two-carbon b ...[more]

PMID: 20300508

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