Synthesis

Synthesis and Olfactory Evaluation of (4aR*, 8aR*)-1, 1, 8a-Trimethyldecahydronaphthalen-4a-ol: A cis-Decalol Intersection Structure of (-)-Patchoulol and (5R*, 6S*)- …

A Jahnke, C Burschka, R Tacke, P Kraft

Index: Jahnke, Astrid; Burschka, Christian; Tacke, Reinhold; Kraft, Philip Synthesis, 2009 , # 1 p. 62 - 68

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Citation Number: 3

Abstract

Abstract Superposition analysis of (-)-patchoulol (1) and the spirocyclic patchouli odorant (5R*, 6S*)-1, 1, 6-trimethylspiro [4.5] decan-6-ol (3) suggested the intersection structure (4aS*, 8aS*)-1, 1, 8a-trimethyldecahydronaphthalen-4a-ol (4) as potential patchouli odorant. The synthesis commenced with the Robinson annulation of mesityl oxide with 2- cyanocyclohexanone, accessible by intramolecular cyclization of pimelonitrile. Weitz- ...

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