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Concise Total Synthesis of Agarozizanol B via a Strained Photocascade Intermediate.

ABSTRACT: The prezizane-type sesquiterpene agarozizanol B was synthesized employing a photochemical cascade reaction as the key step. Starting from a readily available 1-indanone with a tethered olefin, a strained tetracyclic skeleton was assembled which contained all carbon atoms of the sesquiterpene with the correct relative configuration. The conversion into the tricyclic prezizane skeleton was accomplished by a strategic cyclopropane bond cleavage. Prior to the cyclopropane ring opening an adaption of the oxidation state was required, which could be combined with a reductive resolution step. After removal of two functional groups, the natural product was obtained both in racemic form or, if resolved, as the (+)-enantiomer which was shown to be identical to the natural product.

SUBMITTER: Rauscher N

PROVIDER: S-EPMC8596452 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Concise Total Synthesis of Agarozizanol B via a Strained Photocascade Intermediate.

Rauscher Niklas N Naesborg Line L Jandl Christian C Bach Thorsten T

Angewandte Chemie (International ed. in English) 20211005 45

The prezizane-type sesquiterpene agarozizanol B was synthesized employing a photochemical cascade reaction as the key step. Starting from a readily available 1-indanone with a tethered olefin, a strained tetracyclic skeleton was assembled which contained all carbon atoms of the sesquiterpene with the correct relative configuration. The conversion into the tricyclic prezizane skeleton was accomplished by a strategic cyclopropane bond cleavage. Prior to the cyclopropane ring opening an adaption of ...[more]

PMID: 34519408

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