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Efforts toward the Total Synthesis of Elisabethin A.

ABSTRACT: We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cyclization under Mitsunobu conditions as a key step. It allowed the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained from an "underdeveloped" Claisen rearrangement of an aryl dienyl ether.

SUBMITTER: Kaiser M

PROVIDER: S-EPMC9680034 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Efforts toward the Total Synthesis of Elisabethin A.

Kaiser Maximilian M Schönbauer David D Schragl Katharina K Weil Matthias M Gaertner Peter P Enev Valentin S VS

The Journal of organic chemistry 20221025 22

We describe our efforts toward the total synthesis of the natural product elisabethin A. The first route was guided by the proposed biosynthesis, assembling the 6,6-ring system before forming the five-membered ring including the quaternary carbon. The second approach includes a high yielding cyclization under Mitsunobu conditions as a key step. It allowed the preparation of an unusual and highly functionalized bicyclic 6,5-spiro compound. Both routes share a common advanced precursor obtained fr ...[more]

PMID: 36283031

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