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Stereoselective total syntheses of (±)-1,14-herbertenediol and (±)-tochuinyl acetate and facile total syntheses of (±)-α-herbertenol, (±)-β-herbertenol and (±)-1,4-cuparenediol

✍ Scribed by Tapas Paul; Ashutosh Pal; Pranab Dutta Gupta; Debabrata Mukherjee

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
266 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

Stereoselective total syntheses of (±)-1,14-herbertenediol ( ) and (±)-tochuinyl acetate (10) and facile total syntheses of (±)-a-herbertenol ( ), (±)-b-herbertenol ( ) and (±)-1,4-cuparenediol (8) have been successfully accomplished involving intramolecular cyclisation of 3-aryl-3-methyl-6-bromohexanoates and in situ methylation of the resulting cyclopentanecarboxylates as the key reactions.

📜 SIMILAR VOLUMES

Total synthesis of (±)-1,13-herbertenedi
Total synthesis of (±)-1,13-herbertenediol, (±)-α-herbertenol and (±)-β-herbertenol
✍ A. Srikrishna; G. Satyanarayana 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 210 KB

Total synthesis of a-herbertenol, b-herbertenol and 1,13-herbertenediol, employing a Claisen rearrangement and ring-closing metathesis as key reactions for the generation of the cyclopentane containing vicinal quaternary carbons, has been described.