1,7-Cyclogermacra-1(10),4-dien-15-al, a sesquiterpene with a novel skeleton, and other sesquiterpenes from Haitian vetiver oil
✍ Scribed by Peter Weyerstahl; Helga Marschall; Ute Splittgerber; Dietmar Wolf
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 388 KB
- Volume
- 15
- Category
- Article
- ISSN
- 0882-5734
No coin nor oath required. For personal study only.
✦ Synopsis
A medium polar part of commercial Haitian vetiver oil was investigated, particularly with regard to carbonyl compounds. The following new natural compounds were characterized by their NMR data: 1,7-cyclogermacra-1(10),4-dien-15-al (1); 10-epi-acor-3-en-5-one (3); 10-epi-acora-3,11-dien-15-al (4); (E)-opposita-4(15),7(11)-dien-12-al (6); 13-nor-opposit-4(15)-en-11-one (8); 7-epi-cis-dracunculifoliol (ax-4(15)-en-7-ol, 11); elema-1,11-dien-15-al (2 epimers, 12a,b); 6,12-epoxyelema-1,3-diene ( 14); eremophila-1(10), 6-dien-12-al (2 epimers, 15a,b); 15-nor-funebran-3-one (24); 7,15-epoxyprezizaane (31); 15-nor-prezizaan-7-one (33); 12-nor-preziza-7(15)-en-2-one (35, presumable structure); prezizaan-15-al (46); cyclocopacamphan-12-al (2 epimers, 57a,b); 5,6-seco-6,7-furoeudesman-5-one (59); 11,12,13-tri-nor-cis-eudesm-5-en-7-one (61a); 11,12,13-tri-nor-cis-eudesma-5,8-dien-7-one (62); 13-nor-eudesm-5-en-11-one (2 epimers, 63a,b); and 13-nortrans-eudesma-4(15),7-dien-11-one (67). Two oxiranes, 13-nor-4,5-epoxyeudesm-6-en-11-one (66) and 13-nor-7,8-epoxy-trans-eudesm-4(15)-en-11-one (68), which were also isolated, might be artefacts. The polar part of the oil was converted to the methyl ethers. Distillative and chromatographic separation furnished, among others, bfunebrenyl methyl ether 23 H , prezizaenyl methyl ether 50 H , khusimyl methyl ether 51 H , and cyclocopacamphanyl methyl ethers 58a H ,b H (epimers). Thus, the existence of the new alcohols b-funebren-14-ol (23) and prezizaen-12-ol (50) was established. The formerly described con®gurations of the prezizaane derivatives jinkohol, jinkohol II and jinkoholic acid are formulated as the 2-epi-compounds 45, 48 and 49.