Organic Letters, volume 13, issue 21, pages 5748-5750

Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence

Katie Anderson ¹

Frederick Calo ¹

Toni Pfaffeneder ¹

Andrew C White ¹

Anthony A. Barrett ¹

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Department of Chemistry, Imperial College, London, SW7 2AZ, England, United Kingdom |

Publication type: Journal Article

Publication date: 2011-09-21

American Chemical Society (ACS)

Journal: Organic Letters

scimago Q1

SJR: 1.245

CiteScore: 9.3

Impact factor: 4.9

ISSN: 15237060, 15237052

DOI: 10.1021/ol202320m

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PubMed ID: 21936533

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.

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Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

SJR

1.245

CiteScore

9.3

Impact factor

4.9

ISSN

15237060 (Print)

15237052 (Electronic)

Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence

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