Davanone, a key sesquiterpene component of davana oil, has been synthesized in five convenient steps. Oxygenated sesquiterpenes have been linked to insect deterrent properties. Based on initial screening of davana oil, davanone and its hydroxy precursors have been generated and are being evaluated as arthropod deterrents against disease vectors.
HusainA, ViramaniOP, SharmaA, KumarA, MisraLN (1988) Major essential oil bearing plants in India. CIMAP, Lucknow, 167–181.
2.
GulatiBC, KhanMNA. (1980) Essential oil of Artemesia pallens Wall (Davana): a study of minor constituents. Perfume Flavor, 5, 23–24;
3.
KlimesI, LamparskyD. (1986) Analytical results concerning the essential oil of Artemesia pallens (Wall). In Progress in essential oil research. BrunkeEJ. (Ed). Walter de Gruyter, Berlin, 197–214;
CatalanCAN, Del CuencaM, VergheseJ, JoyMT, GuturrezAB, HerzW. (1990) Sesquiterpene ketones related to davanone from Artemesia pallens. Phytochemistry, 29, 2702–2703;
6.
MisraLN, ChandraA, ThakurRS. (1991) Fragrant components of oil from Artemisia pallens. Phytochemistry, 30, 549–552
7.
ThomasAF, PittonG. (1971) The isolation, structure and synthesis of davana ether, an odouriferous compound of the oil of Artemisia pallens Wall. Helvetica Chimica Acta, 54, 1890–1891;
8.
ThomasAF, ThommenW, WillhalmB, HagamanEW, WenkertE. (1974) Terpenoids derived from linalyl oxide. Part 1. The stereochemistry of the davanones. Helvetica Chimica Acta, 57, 2055–2061.
9.
HondaY, OriA, TsuchihashiG. (1987) Stereoselective synthesis of (+) davanone and (+) artemone via anti-selective epoxidation and iodo-cyclization. Chemistry Letters, 16, 1259–1262;
10.
MolanderGA, HarrisJ. (1999) Total synthesis of (±)-davanone. Tetrahedron, 55, 617–624;
11.
MorrisonKC, LitzJP, ScherpelzKP, DossaPD, VosburgDA. (2009) A concise, biomimetic total synthesis of (+)-davanone. Organic Letters, 11, 2217–2218;
12.
SabithaG, PrasadMN, BhikshapathiM, YadavJS. (2010) Stereospecific total synthesis of (+)- davana acid, (+)-nordavanone and (+)- davanone. Synthesis, 5, 807–810;
13.
WanKK, Evans-KlockCD, FielderBC, VosburgDA. (2013) Synthesis of cis- and trans-davanoids: artemone, hydroxydavanone, isodavanone and nordavanone. Synthesis, 45, 1541–1545.
14.
VajsV, TrifunovicS, JanackovicP, SokovicM, MilosavljevicS, TesevicV. (2004) Antifungal activity of davanone-type sesquiterpenes from Artemesia lobelii var. conescens. Journal of the Serbian Chemical Society, 69, 969–972.
15.
PerfumiM, PaparelliF, CingolaniML. (1995) Spasmolytic activity of essential oil of Artemisia thuscula Cav. from the Canary Islands. Journal of Essential Oil Research, 7, 387–392.
VidariG, RosaAD, ZanoniG, BicchiC. (1999) Enantioselective synthesis of each stereoisomer of the pyranoid linalool oxides: the linalool route. Tetrahedron: Asymmetry, 10, 3547–3557.
18.
KreckM, PüschelS, WüstM, MosandlA. (2003) Biogenetic studies in Syringa vulgaris L.: synthesis and bioconversion of deuterium- labeled precursors into lilac aldehydes and lilac alcohols. Journal of Agricultural and Food Chemistry, 51, 463–469.
19.
NageliP, KlimesJ, WeberG. (1970) Structure and synthesis of artemone. Tetrahedron Letters, 57, 5021–5024.
20.
JimenezT, MorcilloSP, Martin-LasantaA, Collado-SanzD, CardenasDJ, GansauerA, JusticiaJ, CuervaJM. (2012) Combining the power of TiIII-mediated processes for easy access to hydroxylated polycyclic terpenoids: synthesis of sesterstatin 1 and C-D rings of aspergilloxide. Chemistry A European Journal, 18, 12825–12833.
21.
ChauhanKR, KlunJR, DebbounM, KramerM. (2005) Repellent efficacy of catnip oil components compared to synthetic amides in human-volunteer laboratory assays against Aedes aegypti (L.). Journal of Medical Entomology, 42, 643–646.