106622-48-4Relevant academic research and scientific papers
An alternative route to (±)-warburganal synthon
Banerjee,Khalil,Vera
, p. 4375 - 4385 (2000)
The transformation of the ketone (1) to the unsaturated diester (11) a potential intermediate for the warburganal (12) is described. The Wittig reaction of theketone (1) with methylenetriphenylphosphorane afforded the olefin (2) which reacts with Woodward
Protective effects of polygodial and related compounds on ethanol-induced gastric mucosal lesions in rats: Structural requirements and mode of action
Matsuda, Hisashi,Pongpiriyadacha, Yutana,Morikawa, Toshio,Kashima, Yousuke,Nakano, Kyoko,Yoshikawa, Masayuki
, p. 477 - 482 (2002)
The methanolic extract from the leaves of Tasmannia lanceolata was found to potently inhibit ethanol-induced gastric lesions in rats. Through bioassay-guided separation, three known sesquiterpenes, polygodial, polygodial 12α-acetal, and polygodial 12β-acetal, and a new sesquiterpene, methyl isodrimeninol, were isolated as the active constituents. Among them, polygodial showed very potent gastroprotective effects (ED50=0.028 mg/kg, po). From the gastroprotective effects of various reduction and oxidation derivatives of polygodial, the dialdehyde or diacetal structure was found to be essential for the strong activity. Since the gastroprotection of polygodial was attenuated by pretreatment with indomethacin, N-ethylmaleimide, NG-nitro-L-arginine methyl ester and ruthenium red, endogenous prostaglandins, sulfhydryl compounds, nitric oxide and vanilloid receptors may be involved in the protective activity.
66. Stereoselectivity of Dienamine Cycloadditions. Synthesis of Functionalised Decalins and Drimanes
Snowden, Roger L.,Brauchli, Robert,Wuest, Manfred
, p. 640 - 651 (2007/10/02)
The cycloaddition stereoselectivity of dienamines 1-4 with dimethyl fumarate and fumaronitrile has been investigated, and functionalised decalins 21-40 have been prepared by elimination of Me2NH from cycloadducts 7-11 and 15-20; in the context of the synthesis of drimane sesquiterpenes, the reduction of dienediesters 29 and 30 is also described.
SYNTHESIS OF BOTH THE ENANTIOMERS OF POLYGODIAL, AN INSECT ANTIFEEDANT SESQUITERPENE
Mori, Kenji,Watanabe, Hidenori
, p. 273 - 282 (2007/10/02)
Both the natural and unnatural enantiomers of polygodial, an insect antifeedant sesquiterpene of the drimane family, were synthesized starting from (S)-3-hydroxy-2,2-dimethylcyclohexanone as a single chiral source.
Synthesis of all possible stereoisomers of polygodial
Guillerm, D.,Delarue, M.,Jalali-Naini, M.,Lemaitre, P.,Lallemand, J.-Y.
, p. 1043 - 1046 (2007/10/02)
The three possible isomers of polygodial, epimers at C-9, cis and trans fused, are described.Controlled kinetic and thermodynamic epimerizations allow preparation of all stereoisomers from the same key intermediate.
SYNTHESE TOTALE DU (+/-)POLIGODIAL, DE LA DRIMENINE ET DE COMPOSES APPARENTES A JONCTION DE CYCLE cis ET trans
Jalali-Naini, M.,Guillerm, D.,Lallemand, J-Y.
, p. 749 - 758 (2007/10/02)
Isomerization by base under kinetic or thermodynamic control of the Diels-Alder adduct of 1,3,3-trimethyl-2-vinyl-1-cyclohexene with dimethyl acetylene dicarboxylate leads to two isomers which, after catalytic hydrogenation, give in high yield starting materials for synthesis of trans and cis drimanes.A short total synthesis of (+/-)-polygodial and (+/-)-drimenine from one of these isomers is desribed.
The Diels-Alder Route to Drimane related Sesquiterpenes; Synthesis of Cinnamolide, Polygodial, Isodrimeninol, Drimenin and Warburganal
Hollinshead, David M.,Howell, S. Christopher,Ley, Steven V.,Mahon, Michael,Ratcliffe, Norman M.,Worthington, Paul A.
, p. 1579 - 1589 (2007/10/02)
The stereospecific preparation of various 1-vinyl-2,6,6-trimethylcyclohex-1-enes (6) as potential diene precursors in the Diels-Alder reaction with dimethyl acetylenedicarboxylate have been investigated.The reaction of the parent diene (6a) with dimethyl acetylenedicarboxylate affords an adduct (18) in 94percent yield.This species was reductively isomerised using 10percent Pd/C/H2 and a mineral acid to give a trans-fused decalin diester (19).Reduction of (19) with lithium aluminium hydride afforded 1,4,4a,5,6,8,8a-octahydro-5,8,8a-trimethyl-1β,4aα,8aβ-naphthalene-1,2-dimethanol (24) a key starting material for the highly efficient syntheses of five drimane sesquiterpene natural products, cinnamolide (1), polygodial (2), isodrimeninol (3), drimenin (4), and warbuganal (5).Microbial oxidation reactions using C. elegans or A. niger of (2), (24), and (1) gave good yields of the corresponding 3β-hydroxy derivatives, (30), (31), and (32).Several other unusually substituted drimane derivatives are reported.
EFFICIENT TOTAL SYNTHESES OF POLYGODIAL AND DRIMENIN.
Jallali-Naini, M.,Boussac, G.,Lemaitre, P.,Larcheveque, M.,Guillerm, D.,Lallemand, J-Y
, p. 2995 - 2998 (2007/10/02)
A short and stereoselective total synthesis of (+/-) polygodial and drimenin is presented.The efficiency of the synthesis is due to the easy access to intermediate diol 4 and its successful direct oxidation into polygodial.
Synthesis of Cinnamolide and Polygodial
Howell, S. Christopher,Ley, Steven V.,Mahon, Michael,Worthington, Paul A.
, p. 507 - 508 (2007/10/02)
Starting from 2,6,6-trimethyl-1-vinylcyclohex-1-ene a short synthesis of the sesquiterpenes cinnamolide and polygodial has been achieved with 60 percent and 57 percent overall yields, respectively.
