Synthesis in the Isocamphane Series, XXVII. Analogues of 4δ-Santalol, I

Article abstract of DOI:10.1007/BF00809950

The synthesis of 4-(3,3-dimethyl-2-exo-norbornyl)-2-methyl-2-buten-1-ol (5), an analogue of δ-santalol (1) has been described.One route to 5 starts with isocamphenilanyl propionic acid (8) which can be prepared in 4 steps from isocamphenilanic acid (9).Also 4 steps lead from 8 to the target molecule 5 with an overall yield of 24percent.By a second and more convergent route, starting from the very easily obtainable bicyclic ketone 19, the allylic alcohol 5 could be obtained again in 4 steps, but this time with an overall yield of 1.3percent.A new and easy synthesis of isocamphenilanyl acetic acid (15), a potential starting material to 5, has been described, also the preparation of some new isocamphane derivatives. - Keywords: Aldol Reaction; Allylic alcohol; Allylic oxidation; 1,2-bis-(3,3-Dimethyl-2-exo-norbornyl)-ethane; 4-(3,3-Dimethyl-2-exo-norbornyl)-2-methylbut-2-en-1-ol; Isocamphane derivatives; Isocamphenilanyl acetic acid; Odour; Selenium dioxode