A concise and scalable strategy for the total synthesis of dictyodendrin B based on sequential C-H functionalization.

Pitts, Andrew K; O'Hara, Fionn; Snell, Robert H; Gaunt, Matthew J

A concise and scalable strategy for the total synthesis of dictyodendrin B based on sequential C-H functionalization.

Repository URI

https://www.repository.cam.ac.uk/handle/1810/248954

Files

Pitts et al 2015 Angewandte Chemie International Edition.pdf (1.11 MB)

Type

Article

Authors

Pitts, Andrew K

O'Hara, Fionn

Snell, Robert H

Gaunt, Matthew J

Abstract

A sequential CH functionalization strategy for the synthesis of the marine alkaloid dictyodendrin B is reported. Our synthesis begins from commercially available 4-bromoindole and involves six direct functionalizations around the heteroarene core as part of a gram-scale strategy towards the natural product.

Keywords

CH functionalization, flow chemistry, metal catalysis, natural products, total synthesis, Carbazoles, Chemistry Techniques, Synthetic, Hydrogen Bonding, Indoles, Molecular Structure, Pyrroles

Journal Title

Angew Chem Int Ed Engl

Journal ISSN

1433-7851
1521-3773

Volume Title

54

Publisher

Wiley

Publisher DOI

https://doi.org/10.1002/anie.201500067

Rights

http://www.rioxx.net/licenses/all-rights-reserved

Sponsorship

Engineering and Physical Sciences Research Council (EP/I00548X/1)

We are grateful to AstraZeneca, Pfizer, and EPSRC (A.K.P., F.O. and R.H.S.) and the ERC and EPSRC for fellowships (M.J.G.).

Collections

Scholarly Works - Chemistry
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