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Concise Total Synthesis of Herqulines B and C.

ABSTRACT: A simple total synthesis of herqulines B and C is reported, modeled on the reductive biosynthesis reported previously by other researchers. Commencing from tyrosine, these alkaloids were fashioned through a dimerization, macrocyclization, and four consecutive reductions. Emerging from these studies are strategic insights on the synthesis of these strained alkaloids, as well as mild conditions for the exhaustive reduction of diketopiperizines.

SUBMITTER: He C

PROVIDER: S-EPMC6475496 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Concise Total Synthesis of Herqulines B and C.

He Chi C He Chi C Stratton Thomas P TP Baran Phil S PS

Journal of the American Chemical Society 20181224 1

A simple total synthesis of herqulines B and C is reported, modeled on the reductive biosynthesis reported previously by other researchers. Commencing from tyrosine, these alkaloids were fashioned through a dimerization, macrocyclization, and four consecutive reductions. Emerging from these studies are strategic insights on the synthesis of these strained alkaloids, as well as mild conditions for the exhaustive reduction of diketopiperizines. ...[more]

PMID: 30575396

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