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Synthesis of the racemic tetracyclic core of CP-225,917—a model compound lacking the sidearms of the natural product

✍ Scribed by Derrick L.J Clive; Shaoyi Sun

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
152 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Compound 3, representing the tetracyclic core structure of CP-225,917, was prepared from bridgehead olefin 9, which was first converted into ketone 13. Peterson olefination then gave 15, and this was elaborated into the anhydride 19, from which crystalline 3 was reached by a sequence of deprotection and oxidation steps.

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✍ Derrick L. J. Clive; Shaoyi Sun 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 26 KB 👁 2 views

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Norbornene was converted via diketone 23 into the strained lactone 27; this was rearranged thermally to lactone 28, from which point the complete oxygenated core of CP-225,917 is accessible by deprotection and oxidation steps, including a new method for converting a furan system into a hydroxy buten