## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a βFull Textβ option. The original article is trackable v
A short total synthesis of estrone derivatives: A novel 1,3-rearrangement of an allylic nitro group
β Scribed by Bernard Barlaam; Jean Boivin; Laurent Elkaim; Sarah Elton-Farr; Samir Z. Zard
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- French
- Weight
- 626 KB
- Volume
- 51
- Category
- Article
- ISSN
- 0040-4020
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## Methyl 4-(5-nitro-1,3-dioxaspiro[5.5] undecan-5-yl)but-2-enoate 2, obtained from the palladium(0)-catalyzed reaction of a salt of 5-nitro-1,3-dioxane 1 with methyl g-bromocrotonate, was converted into the title piperidinone (ee 78%) in three steps.
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