73374-47-7Relevant academic research and scientific papers
Total synthesis of maoecrystal v
Zhang, Wei-Bin,Lin, Guang,Shao, Wen-Bin,Gong, Jian-Xian,Yang, Zhen
supporting information, p. 903 - 909 (2015/04/14)
Maoecrystal V (1) is a novel diterpenoid, which was originally isolated from the leaves of the Chinese medicinal herb Isodon eriocalyx in 2004 by Sun etal.1 It has been found to be selectively cytotoxic towards HeLa cells, with an IC50 value of 20ng mL-1. Significant research efforts have been devoted to the synthesis of maoecrystal V because of its intriguing biological properties, rarity in nature, and complex structural features. Herein, we describe our recent investigations, which have culminated in the total synthesis of (±)-maoecrystal V. The current strategy involved three key steps for the successful construction of the key tetrahydrofuran oxa-bridge skeleton, including a Wessely oxidative dearomatization, a novel intramolecular Diels-Alder reaction, and a RhII-catalyzed O-H insertion reaction.
Isomerisation of 2,2-dimethyl dimedone to (D,L) cis-chrysanthemic acid
Krief, Alain,Lorvelec, Guillaume,Jeanmart, Stephane
, p. 3871 - 3874 (2007/10/03)
(D,L) cis-Chrysanthemic acid has been obtained in four steps from 2,2- dimethyl dimedone which involves Bamford-Stevens olefination and tandem cyclization-Grob fragmentation reactions. (C) 2000 Published by Elsevier Science Ltd.
Ring Expansion of Cyclenones: an Unusual Regioselectivity
Krief, A.,Laboureur, J. L.
, p. 702 - 704 (2007/10/02)
Various cyclenones have been homologated by a two-step sequence involving a reaction with α-selenoalkyl-lithium compounds and further reaction of the resulting β-hydroxyselenides with thallium(I) ethoxide in chloroform; an unusually high propensity of the
THE PALLADIUM (II) ACETATE PROMOTED 6-ENDO-TRIG CYCLIZATION OF 1,1-DIALKYL-2-SILYLOXY-1,5-DIENES.
Torres, Luz E.,Larson, Gerald L.
, p. 2223 - 2226 (2007/10/02)
A route to cyclohexenones via the treatment of selected γ,δ-unsaturated enol silyl ethers with palladium (II) acetate is presented.
Optical Rotatory Dispersion Studies. 138. Synthesis and Conformational Analysis of β-Heteroatom-Substituted Cyclohexanones
Gorthey, Lee Ann,Vairamani, Mariappandar,Djerassi, Carl
, p. 4173 - 4182 (2007/10/02)
Circular dichroism and proton magnetic resonance spectroscopy were used in the conformational analysis of a series of β-heteroatom-substituted cyclohexanones.It was found that the axial population of the substituted ketone relative to that of the monosubstituted cyclohexanone is enhanced for the more highly electronegative substituents oxygen and fluorine and decreased for the less electronegative substituents chlorine, bromine, and sulfur.Possible mechanisms underlying this behavior, including electrostatic and dipole-dipole interactions as well as through-space and through-bond orbital interactions, are briefly discussed.
