Synthesis ofrac-Bisabola-3(15),10-dien-7-ol
✍ Scribed by Weyerstahl, Peter ;Schlicht, Volker
- Publisher
- John Wiley and Sons
- Year
- 1997
- Tongue
- English
- Weight
- 199 KB
- Volume
- 1997
- Category
- Article
- ISSN
- 0947-3440
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
1‐Acetyl‐4‐methylenecyclohexane (6) was obtained from ethyl 4‐methylenecyclohexane carboxylate (2), by DIBAH reduction (→ 4), Grignard reaction (→ 5) and oxidation. A further Grignard reaction furnished the rac‐bisabola‐3(15),10‐dien‐7‐ol (1), which we isolated recently from Vetiver oil. Its odor is mainly aldehydic (fatty, floral).
📜 SIMILAR VOLUMES
## Abstract The synthesis of kempa‐6,8‐dien‐3__β__‐ol (**4a**), as a synthetic leading model of the natural product **4b**, was carried out starting from intermediate **12**, the synthetic route of which has been developed previously (__Scheme 1__). The conversion of **12** to the model compound **
Treatment of 3~.benzoyloxy-140, 15wepoxy-5(~.cholesg-7-ene with boron trifluoride-etherate 8ave, in 43% yield, 30-benzoyloxy-Sa, 14~cholest-7-en,15-one with the unnatt~ral C-D ring juncture, Reduction of the latteg compound with lithium aluminum hydride gave 15a, 14O-~holest-7.en'3p, 15wdiol and 5~,
Stereospecific synthesis of a common precursor of several acyclic (2R,3S)-2-amino-3-ols from marine origin, especially of (2R,3S)-2-amino-tetradeca-5,7-dien-3-ol isolated from Xestospongia sp., is described starting from the versatile epoxide 10.
The synthesis of "09R#!"E#!acora!2\6"00#!dien!01!al "0# is described starting from the enanti! omerically pure "¦#!pulegenic acid "3# via the Diels!Alder adducts 7a\b[ The odour of the new sesquiterpene aldehyde was typically aldehydic\ fruity and leathery[