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Stereoselective synthesis of trans-hydrindanes by internal vinylsilane acylation

✍ Scribed by Kentaro Fukuzaki; Eiichi Nakamura; Isao Kuwajima

Book ID
104242275
Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
238 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

Sumsrary: trans-Hydrindanediones (1, 3, and 15) have been synthesized in short steps through stereoselective introduction of vinylsilane units onto the cycloalkenones 5 OK 10 followed by AgBF4-mediated internal acylation of the vinylsilane moiety.

We report here two of our syntheses of functionalized trans-hydrindanes (1, 3, and 15) that we have developed in conjunction with the projected steroid synthesis.' These approaches rely, in common, on an intramolecular acylation reaction of vinylsilanes 2 as the crucial ring forming reaction. The first approach, as shown in Scheme I, utilizes the reaction for the C ring construction, and the second one for

πŸ“œ SIMILAR VOLUMES

A β€œtunable” stereoselective alkene synth
A β€œtunable” stereoselective alkene synthesis by iododesilylation of vinylsilanes
✍ T.H. Chan; K. Koumaglo πŸ“‚ Article πŸ“… 1986 πŸ› Elsevier Science 🌐 French βš– 202 KB

The stereoselectivity of iododesilylation of terminal E-vinylsilanes varies with changing amount of Lewis acid. The use of this "tunable" stereoselective reaction was demonstrated by the syntheses of two insect sex pheromones with defined E/Z isomeric ratios.