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Ester Dienolate [2,3]-Wittig Rearrangement in Natural Product Synthesis: Diastereoselective Total Synthesis of the Triester of Viridiofungin A, A 2 , and A 4

✍ Scribed by Pollex, Annett; Millet, Agnès; Müller, Jana; Hiersemann, Martin; Abraham, Lars


Book ID
126909485
Publisher
American Chemical Society
Year
2005
Tongue
English
Weight
300 KB
Volume
70
Category
Article
ISSN
0022-3263

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✍ E.Kate Dorling; Andrew P. Thomas; Eric J. Thomas 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 119 KB

The relative configurations of 1,8-stereogenic centres can be controlled by coupling the tin(IV) chloride promoted reactions of aldehydes with 4-alkoxypent-2-enylstannanes, which proceed with excellent 1,5-induction, with a 2,3-Wittig rearrangement: this approach has been used to complete a diastere