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The chemistry of thujone. VI. Thujone as a chiral synthon for the synthesis of optically active steroid analogues

✍ Scribed by James P. Kutney; Peter Grice; Keith O. Pascoe; Krystyna Piotrowska; Steven J. Rettig; Jerzy Szykula; James Trotter


Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
562 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

The thujone derived enone 1 is converted in one step to the pentacyclic compound 4. The structure of 4 was determined by X‐ray diffraction analysis. The acid‐catalyzed cyclopropane‐ring opening of 4 and of the model compound 9 are described.


📜 SIMILAR VOLUMES


The chemistry of thujone. IX. Thujone as
✍ James P. Kutney; Peter Grice; Krystyna Piotrowska; Steven J. Rettig; Jerzy Szyku 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 432 KB

## Abstract The thujone‐derived enone **1**, upon base‐catalyzed reaction with 2‐methyl‐6‐vinylpyridine is converted to the pyridine analogue **5** __(Scheme 1)__. Catalytic reduction of the latter to **6** generates two new centers of chirality which eventually become C(8) and C(14) in the ultimat

The chemistry of thujone. VIII. Thujone
✍ James P. Kutney; Peter Grice; Keith O. Pascoe; Krystyna Piotrowska; Steven J. Re 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 857 KB

## Abstract The thujone‐derived enone **1** is converted __via__ enol lactone intermediates **4** and **5** to the optically active steroidal analogue **13** and the corresponding 19‐norsteroid analogue **14**. The structure of **13** was determined by X‐ray diffraction analysis. The acid‐catalyzed