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Stereocontrolled synthesis of either (22S)- or (22R)-hydroxy-23-acetylenic steroid side chains via [2,3]-Wittig sigmatropic rearrangement

✍ Scribed by Kōichi Mikami; Kazuya Kawamoto; Takeshi Nakai


Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
219 KB
Volume
26
Category
Article
ISSN
0040-4039

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📜 SIMILAR VOLUMES


Application of [2,3]Wittig and [3,3]Clai
✍ Ko¯lchi Mikami; Kazuya Kawamoto; Takeshi Nakai 📂 Article 📅 1986 🏛 Elsevier Science 🌐 French ⚖ 216 KB

An efficient approach to either (22S)-or (22Ij)-hydroxy-23-carboxylic is described which relies on the stereochemical transmission via [2,3]Wittig sigmatropic rearrangement, respectively. acid side chain or [3,3]Claisen

Diastereocontrol via lewis acid-promoted
✍ Kōichi Mikami; Teck-Peng Loh; Takeshi Nakai 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 213 KB

Taking the judicious choice of the Lewis acid employed, the glyoxylate ene reactions are shown to proceed with a high level of either erythro or threo diastereoselection. The utility of the ene methodology is demonstrated through the stereocontrolled synthesis of a 22F&hydroxy-23-carboxylate steroid