A Concise and Scalable Strategy for the Total Synthesis of Dictyodendrin B Based on Sequential CH Functionalization

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...

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Bibliographic Details
Published inAngewandte Chemie (International ed.) Vol. 54; no. 18; pp. 5451 - 5455
Main Authors Pitts, Andrew K., O'Hara, Fionn, Snell, Robert H., Gaunt, Matthew J.
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 27.04.2015
WILEY‐VCH Verlag
Wiley
Subjects
Carbazoles - chemical synthesis
Carbazoles - chemistry
Chemistry
Chemistry Techniques, Synthetic
Chemistry, Multidisciplinary
CH functionalization
flow chemistry
Hydrogen Bonding
Indoles - chemistry
metal catalysis
Molecular Structure
natural products
Physical Sciences
Pyrroles - chemical synthesis
Pyrroles - chemistry
Science & Technology
total synthesis
ROUTES
TELOMERASE
NATURAL-PRODUCTS
BOND FUNCTIONALIZATION
CARBAZOLES
C-H functionalization
INDOLES
natural products
SPONGE
total synthesis
INHIBITORS
FACILE
metal catalysis
ALKENYLATION
flow chemistry
CH functionalization
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Summary: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. One by one: A sequential CH functionalization strategy for the synthesis of the marine alkaloid dictyodendrin B is reported. The synthetic route 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.
Bibliography:ark:/67375/WNG-6JM2QDK6-8
istex:CFCB5B9EBC74F9E1B34E555EC901AEE7717E50C3
Pfizer
ERC
EPSRC
AstraZeneca
We are grateful to AstraZeneca, Pfizer, and the EPSRC (A.K.P., F.O., R.H.S., and M.J.G.) and the ERC (M.J.G.) for fellowships. Mass spectrometry data were acquired at the EPSRC UK National Mass Spectrometry Facility at Swansea University. X-ray crystallography data was collected and solved by Peter D. Matthews. We are grateful to Phillip Murray and Prof. Steven V. Ley for assistance with and advice on flow chemistry. We also acknowledge Dr. Johan Kajanus (AstraZeneca) and Dr. Abid Massood (Pfizer) for useful discussions.
ArticleID:ANIE201500067
We are grateful to AstraZeneca, Pfizer, and the EPSRC (A.K.P., F.O., R.H.S., and M.J.G.) and the ERC (M.J.G.) for fellowships. Mass spectrometry data were acquired at the EPSRC UK National Mass Spectrometry Facility at Swansea University. X‐ray crystallography data was collected and solved by Peter D. Matthews. We are grateful to Phillip Murray and Prof. Steven V. Ley for assistance with and advice on flow chemistry. We also acknowledge Dr. Johan Kajanus (AstraZeneca) and Dr. Abid Massood (Pfizer) for useful discussions.
These authors contributed equally to this work.
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UKRI
ObjectType-Article-1
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ObjectType-Feature-2
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201500067