Development of an enolate alkynylation approach towards the synthesis of the taiwanschirin natural products

Through the use of model studies, an approach was conceived towards the synthesis of the taiwanschirin family of natural products. These are structurally complex compounds which represent highly challenging and biologically active targets for total synthesis. This work describes a successful synthes...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2021-10, Vol.12 (4), p.13392-13397
Main Authors: Haughey, Maxwell B, Christensen, Kirsten E, Poole, Darren L, Donohoe, Timothy J
Format: Article
Language:English
Subjects:
Chemistry
Complex compounds
Natural products
Synthesis
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Summary:Through the use of model studies, an approach was conceived towards the synthesis of the taiwanschirin family of natural products. These are structurally complex compounds which represent highly challenging and biologically active targets for total synthesis. This work describes a successful synthesis of the complex taiwanschirin fused [8,6,5] core through a novel alkynylation reaction coupled with an intramolecular Heck reaction used to construct the 8-membered ring. Key enolate alkynylation and ring closing Heck reactions have been used to make the core of the taiwanschirin natural products.
ISSN:2041-6520
2041-6539
DOI:10.1039/d1sc04247e