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1,8-Stereocontrol by 1,5-induction using an allylstannane followed by a 2,3-Wittig rearrangement: Diastereoselective total synthesis of (±)-epipatulolide C

✍ Scribed by E.Kate Dorling; Andrew P. Thomas; Eric J. Thomas

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
119 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 diastereoselective synthesis of (+)-epipatulolide C 16.

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1,8-Stereocontrol by 1,5-induction using an allylstannane followed by Ireland-Claisen rearrangement: Diastereoselective total synthesis of (±)-patulolide C
✍ E. Kate Dorling; Eric J. Thomas 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 223 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 an Ireland-Claisen rearrangement: this approach has been used to complete a di