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Synthesis of a spirovetivane intermediate: a problem in carbonyl transposition

✍ Scribed by K.P. Subrahamanian; William Reusch

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
185 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

The spiro[4.5]decane ring system, which is found in sesquiterpenes of the spirovetivane class has been the target of many syntheses. Over the past eight years at least eight total syntheses of B-vetivone (,+) and more than five of hinesol ( 2) have been recordedl. -0 * =4%-Marshall's landmark synthesis of B-vetivone la proceeded via enone 2, prepared in three step! (36% overall yield) from dienone 2. Other preparations of & have been published 2,3 , but they do not match the original in either convenience or yield.

We recently showed that cyclopropanol J, can be rearranged to spirodiketone 2 in good yield4.

An equivalent rearrangement of the methyl homolog $ serves to generate a7, a potentially useful intermediate in spirovetivane synthesis. We now report the conversion of g into $, a transformation that establishes the structure and configuration of the former.

πŸ“œ SIMILAR VOLUMES

Stereochemical relationships in spirovet
Stereochemical relationships in spirovetivane sesquiterpenes: The total synthesis of hinesol
✍ James A. Marshall; Stephen F. Brady πŸ“‚ Article πŸ“… 1969 πŸ› Elsevier Science 🌐 French βš– 220 KB

Recent synthetic and degradative studies (1) have necessitated a structural revision of the entire class of vetivane sesquiterpenes whereby the previously accepted bicycIoC5.3.01decane carbon framework (I) must be discarded in favor of the spiroC4. Sldecane system (II).

1,2-Carbonyl Transposition of a Protecte
1,2-Carbonyl Transposition of a Protected Rubanone: Stereoselective synthesis of bicyclic and tricyclic lactams derived from quinidine
✍ Jens Frackenpohl; Peter Langer; H. Martin R. Hoffmann πŸ“‚ Article πŸ“… 1998 πŸ› John Wiley and Sons 🌐 German βš– 527 KB

In this work, the usual 1,s-functionality distance of Robinson annulation products was transformed into the required 1,4-dicarbonyl distance. ') The C-atom numbering corresponds to the cinchonan numbering (see Fig. )