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The chemistry of thujone. VIII. Thujone as a chiral synthon for the synthesis of optically active steroid analogues. The enol lactone route

✍ 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
1983
Tongue
German
Weight
857 KB
Volume
66
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 cyclopropane‐ring opening of 13 and ozonolysis of the resulting olefin provided the 16‐keto‐steroid analogue 18.

📜 SIMILAR VOLUMES

The chemistry of thujone. VI. Thujone as
The chemistry of thujone. VI. Thujone as a chiral synthon for the synthesis of optically active steroid analogues
✍ James P. Kutney; Peter Grice; Keith O. Pascoe; Krystyna Piotrowska; Steven J. Re 📂 Article 📅 1982 🏛 John Wiley and Sons 🌐 German ⚖ 562 KB

## 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.

The chemistry of thujone. IX. Thujone as
The chemistry of thujone. IX. Thujone as a chiral synthon for the synthesis of optically active steroid analogues. The vinylpicoline route
✍ 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