Drimanic sesquiterpenes

The isoprenoids contribute most to the list of structural similarities in the sea and on land. They range from common classes in both ecosystems, such as drimane sesquiterpenes, to rare classes in the sea, such as the trichothecenes (Chart 8.3.11). The similarity in marine and terrestrial polyether triterpenes (Chart 8.3.12) may be seen as convergence toward chemically favored structures, starting from squalene as a biosynthetic precursor. Similar conclusions may apply to polycyclic triterpenes. 

Bathydoris hodgsoni can be found in the deep waters of the Weddell Sea. This nudibranch elaborates the drimane sesquiterpene hodgsonal (Structure 7.78) and sequesters it in its mantle tissues.50 164The nudibranch Tritoniella belli collected from McMurdo Sound is the only documented example of an Antarctic mollusc sequestering defensive chemistry from its diet.44 Among the glyceride esters (Structures 7.79-7.81) isolated from this species, chimyl alcohol (Structure 7.79) can also be found in one of its prey items, the stoloniferan coral Clavularia frankliniana. Sequestration of these defensive chemicals is opportunistic, however, and other, still undescribed metabolites are more commonly associated with defense in this mollusc.49... 

Iken, K., Avila, C., Ciavatta, M. L., Fontana, A., and Cimino, G., Hodgsonal, a new drimane sesquiterpene from the mantle of the antarctic nudibranch Bathydoris hodgsoni, Tetrahedron Lett., 39, 5635, 1998. 

Atdehyde-enolate hydroxylation. Enolate hydroxylation has been extended to, the aldehyde 1 by Tanis and Nakanishi in a total synthesis of the drimanic sesquiterpene ( )-warburganal (3). Thus treatment of 1 with LD A in THF at - 78°C followed by M0O5 -HMPT (1.5 equiv.) affords 2 in 85% yield. 

D. Kioy, A. I. Gray and P. G. Waterman, Further drimane sesquiterpenes from the stem bark of Canella winterana, J. Nat. Prod., 52 (1989) 174-177. 

M. S. Al-Said, S. M. El-Khawaja, F. S. El-Feraly and C. H. Hufford, 9-Deoxy drimane sesquiterpenes from Canella winterana. Phytochemistry, 29 (1990) 975-977. 

Hlubucek, J.R., A.J. Aasen, S.O. Almqvist, and C.R. EnzeU Tobacco chemistry. 25. Two new drimane sesquiterpene alcohols from Greek Nicotiana tabacum Acta Chem. Scand. B28 (1974) 289-294. 

Muzigadial (58), a drimane sesquiterpene isolated from the bark of East African plant Warburgia ugandensis and W. stuhlmanii [24,25] shows potent activity against the African armyworms. In addition, muzigadial (58) exhibits a broad antibiotic spectrum as well as helicocidal activity [24]. 

C22H30O3, Mr 342.48, pale yellow cryst., mp. 139-140°C, [a]u -136° (CHClj), soluble in organic solvents. A metabolite from cultures of the phytopath-ogenic fungus Helminthosporium siccans. The strac-ture of S. consists of a drimane sesquiterpene linked to orcinol. S. has broad antifungal activity, especially against Trichophyton species that cause skin infections. 

Ayer, W.A., and L.S. Trifonov Drimane sesquiterpene lactones from Peniophora polygonia. J. Nat. Prod. 55, 1454 (1992). 

Among drimane sesquiterpenes of Lactarius, only uvidin C (3.9) has been chosen so far as a synthetic target. Two syntheses of this compound have been reported as a racemate by Ziegler et al. 148), and as the natural (—)-enantiomer by Cortes and colleagues 149),... 

De Bernardi, M., G. Mellerio, G. Vidari, P. Vita-Finzi, and G. Fronza Fungal Metabolites. Part 5. Uvidins, New Drimane Sesquiterpenes from Lactarius uvidus Fries. J. Chem. Soc. Perkin Trans. I, 221 (1980). 

B. J. M. Jansen, Total Synthesis of Insect Antifeedant Drimane Sesquiterpenes, Ph.D. Thesis, University of Wageningen, 1997. 

Butler. M.S. and Capon, R.J. (1993b) Beyond polygodial new drimane sesquiterpenes from a Southern Australian marine sponge Dysidea sp. Aust.J. Chem., 46,1255-1267. 

Nakano, T, Villamizar, J.E., and Maillo, M.A. (1999) Highly effident synthesis of optically active drimanic sesquiterpenes, (-l-)-ffiegin, (-l-)-epifutronolide (7 -hydroxyisodrimenin) and (-f)-7-ketoisodri-menin. Tetrahedron, 55, 1561-1568. 

Too few pubhcations have appeared for us to offer any generalizations, but the work that has been pubhshed so far shows that species of the genus Onchiddla have yielded only drimane sesquiterpenes, and species of the genus... 

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