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Total synthesis of (±)-dihydroisosubamol

Pflasterer, D, Rudolph, M, Yates, BF ORCID: 0000-0001-9663-3301, Ariafard, A ORCID: 0000-0003-2383-6380 and Hashmi, ASK 2017 , 'Total synthesis of (±)-dihydroisosubamol' , Advanced Synthesis and Catalysis, vol. 359, no. 5 , 866–874 , doi: 10.1002/adsc.201600663.

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Abstract

We herein report the first total synthesis of the dibenzocycloheptanoide (±)-dihydroisosubamol. The key step includes a recently developed gold-catalysed hydroarylation reaction for the construction of the dibenzocycloheptene motif. Additional steps are a Suzuki-Miyaura cross coupling, a palladium-catalysed hydroxylation and an allylic oxidation. To access the saturated seven-membered ring system an iridium-catalysed hydrogenation proved to be successful.

Item Type: Article
Authors/Creators:Pflasterer, D and Rudolph, M and Yates, BF and Ariafard, A and Hashmi, ASK
Keywords: dibenzocycloheptanoides, natural products, total synthesis, dibenzocycloheptenes, gold
Journal or Publication Title: Advanced Synthesis and Catalysis
Publisher: Wiley-V C H Verlag Gmbh
ISSN: 1615-4150
DOI / ID Number: 10.1002/adsc.201600663
Copyright Information:

Copyright 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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