A facile total synthesis of the bisabolane sesquiterpene, xanthorrhizol (1), has been achieved in 6 steps, in 48% overall yield. The starting material was 3-methoxy-4-methyl-phenoacetone (7), and a Claisen-Johnson rearrangement was used as the key step to construct the skeleton of the target molecule.
GarciaGE, MendozaV, GuzmanBA. (1987) Perezone and related sesquiterpenes from parvifolin. Journal of Natural Products, 50, 1055-1058.
2.
ItokawaH, HirayamaF, FunakoshiK, TakeyaK. (1985) Studies on the antitumor bisabolane sesquiterpenoids isolated from Curcuma xanthorrhiza. Chemical & Pharmaceutical Bulletin, 33, 3488-3491.
3.
HwangJ, ShimJ, BaekN, PyunY. (2000) Xanthorrhizol: A potential antibacterial agent from Curcuma xanthorrhiza against Streptococcus mutans. Planta Medica, 66, 196-197.
4.
Ponce-MonterH, CamposMG, AguilarI, DelgadoG. (1999) Effect of xanthorrhizol, xanthorrhizol glycoside and trachylobanoic acid isolated from cachani complex plants upon the contractile activity of uterine smooth muscle. Phytotherapy Research, 13, 202-205.
5.
CamposM, OropezaM, VillanuevaT, AguilarMI, DelgadoG, PonceH. (2000) Xanthorrhizol induces endothelium-independent relaxation of rat thoracic aorta. Life Science, 67, 327-333.
6.
YamazakiM, MaebayashiY, IwaseN, KanekoT. (1988) Studies on pharmacologically active principles from Indonesian crude drugs. I. Principle prolonging pentobarbital-induced sleeping time from Curcuma xanthorrhiza Roxb. Chemical & Pharmaceutical Bulletin, 36, 2070-2074.
7.
SiratHM, HongNM, JauriMH. (2006) Chemistry of xanthorrhizol: synthesis of several bisabolane sesquiterpenoids from xanthorrhizol. Tetrahedron Letters, 48, 457-460.
8.
FugantiC, SerraS. (2000) Baker's yeast-mediated enantioselective synthesis of the bisabolane sesquiterpenes (+)-curcuphenol, (+)-xanthorrhizol, (-)-curcuquinone and (+)-curcuhydroquinone. Journal of the Chemical Society-Perkin Transactions 1, 3758-3764.
9.
NagumoS, IrieS, HayashiK, AkitaH. (1996) A formal total synthesis of xanthorrhizol based on nucleophilic opening of vinyloxirane by arylcopper reagent. Heterocycles, 43, 1175-1178.
10.
SatoK, BandoT, ShindoM, ShishidoK. (1999) An enantiocontrolled total synthesis of (-)-xanthorrhizol. Heterocycles, 50, 11-15.
11.
MeyersAI, StoianovaD. (1997) Short asymmetric synthesis of (+)-α-curcumene and (+)-xanthorrhizol. Journal of Organic Chemistry, 62, 5219-5221.
12.
JesusLma, AdrianCZ, MoisesRO, JoseAzg. (2008) An efficient synthesis of (+/-)-xanthorrhizol. One-pot decyanation and demethylation. Letters in Organic Chemistry, 5, 470-472.
13.
ChavanSP, ThakkarM, KalkoteUR. (2007) An enantiospecific synthesis of (+)-isoparvifolinone and (-)-parvifoline. Tetrahedron Letters, 48, 535-537.
14.
KrauseW, BohlmannF. (1987) Synthesis of hydroxycadalene and hydroxycalamenene via 13-hydroxyxanthorrhizol, a possible precursor of parvifolin. Tetrahedron Letters, 28, 2575-2578.
15.
JohnTK, RaoGsk. (1985) Studies in terpenoids. Part LXIII. Absolute configuration of naturally occurring (-)-xanthorrhizol. Indian Journal of Chemistry, Section B, 24B, 35-37.
16.
MontielLE, ZepedaLG, TamarizJN. (2010) Efficient total synthesis of racemic bisabolane sesquiterpenes curcuphenol and xanthorrhizol starting from substituted acetophenones. Helvetica Chimica Acta, 93, 1261-1273.
17.
JohnsonWS, WerthemannL, BartlettWR, BrocksomTJ, LiT-T, FaulknerDJ, PetersenMR. (1970) Simple stereoselective version of the Claisen rearrangement leading to trans-trisubstituted olefinic bonds. Synthesis of squalene. Journal of the American Chemical Society, 92, 741-743.
