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Total Synthesis of Tagetitoxin.

ABSTRACT: The intriguing structure of tagetitoxin (1), a long-standing challenge in natural product synthesis, has been the subject of multiple revisions and has been confirmed through total synthesis. The route commences from a renewable furan starting material and features a number of unusual transformations (such as rearrangements, bromocyclization, and P(V)-based phosphate installation) to arrive at the target in 15 steps. As the route was designed to enable access to both enantiomers, the absolute configuration of the natural product could be assigned using a bioassay on (+)-1 and (-)-1.

SUBMITTER: He C

PROVIDER: S-EPMC8353664 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Total Synthesis of Tagetitoxin.

He Chi C Chu Hang H Stratton Thomas P TP Kossler David D Eberle Kelly J KJ Flood Dillon T DT Baran Phil S PS

Journal of the American Chemical Society 20200727 32

The intriguing structure of tagetitoxin (<b>1</b>), a long-standing challenge in natural product synthesis, has been the subject of multiple revisions and has been confirmed through total synthesis. The route commences from a renewable furan starting material and features a number of unusual transformations (such as rearrangements, bromocyclization, and P(V)-based phosphate installation) to arrive at the target in 15 steps. As the route was designed to enable access to both enantiomers, the abso ...[more]

PMID: 32687336

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