23538-45-6Relevant academic research and scientific papers
Synthesis of chiloscyphones and the biological activities of their synthetic intermediates against methicillin-resistant Staphylococcus aureus (MRSA)
Shiina, Junichi,Obata, Rika,Tomoda, Hiroshi,Nishiyama, Shigeru
, p. 2362 - 2370 (2007/10/03)
The total syntheses of chiloscyphone (1) and isochiloscyphone (2) have been achieved. Furthermore, the synthetic intermediate 5 shows biological activity against methicillin-resistant Staphyrococcus aureus, and compounds 5, 17, and 18, display imipenem-ty
A new approach to the bicyclo[4.3.0] ring system of natural products from the liverwort: Total synthesis of (±)-chiloscyphone and (±)-isochiloscyphone
Shiina, Junichi,Nishiyama, Shigeru
, p. 9033 - 9036 (2007/10/03)
Tricyclic intermediate 5 was synthesized by using the intramolecular Diels-Alder reaction as the key step. Total synthesis of (±)- chiloscyphone and (±)-isochiloscyphone was accomplished. Construction of the tricyclic derivative 5, a common intermediate f
A new annulation method. Total syntheses of the sesquiterpenoids (+/-)-chiloscyphone and (+/-)-6-epi-chiloscyphone
Piers, Edward,Tse, Hoi Lun Allan
, p. 983 - 994 (2007/10/02)
The efficacy of a new annulation method, developed for the construction of functionalized bicyclic compounds, is illustrated by conversion of the β-keto esters 18 and 19 into the bicyclonon-1-enes 33 and 34, respectively, and by transformation of 2-methoxycarbonylcyclopentanone (20) into the bicyclonon-6-ene 38 and the bicyclodec-7-enes 48 and 51.Application of the method to total syntheses of the structurally unusual sesquiterpenoids (+/-)-chiloscyphone (16) and (+/-)-6-epi-chiloscyphone (17) is described.
Total Synthesis of (-)-Chiloscyphone, Sesquiterpenoid Isolated from the Liverwort. Absolute Configuration of (-)-Chiloscyphone and (+)-Chiloscypholone
Tori, Motoo,Hasebe, Takeshi,Asakawa, Yoshinori
, p. 1706 - 1712 (2007/10/02)
The absolute configurations of (-)-chiloscyphone and (+)-chiloscypholone isolated from the liverwort Chiloscyphus polyanthos and C. pallescens respectively, have been determined by the total synthesis of the optically active compound.The 1,4-addition of v
Absolute Configurations of the Liverwort Sesquiterpenoids, (-)-Chiloscyphone and (+)-Chiloscypholone: Total Synthesis of Optically Active Compounds
Tori, Motoo,Hasebe, Takeshi,Asakawa, Yoshinori
, p. 1552 - 1553 (2007/10/02)
The absolute configurations of(-)-chiloscyphone and (+)-chiloscypholone isolated from the liverworts Chiloscyphus polyanthos and C. pallescens have been determined by the total synthesis of the optically active compounds.The key intermediate alcohol has been resolved by the use of (1S)-(-)-camphanic chloride.
Total Sythesis of Liverwort Sesquiterpene Ketone (+/-)-Chiloscyphone via Intramolecular Aldol Condensation
Tori, Motoo,Hasebe, Takeshi,Asakawa, Yoshinori
, p. 2059 - 2060 (2007/10/02)
(+/-)-Chiloscyphone, a sesquiterpene ketone isolated from the liverwort, has been synthesized starting from 3,4-dimethyl-2-cyclohexen-1-one via intramolecular aldol condensation.
SYNTHESE DES SESQUITERPENS (+/-)-CHILOSCYPHON
Gerling, Klaus-Guenther,Wolf, Herbert
, p. 1293 - 1294 (2007/10/02)
The revised structure of chiloscyphone (1) is confirmed by total synthesis: 4a,b, obtained by stereoselective cyclization of 2, were transformed to 8.Ketone 8 was converted to (+/-)-1 by direct α-methylenation.
