547-15-9Relevant academic research and scientific papers
First total synthesis and assignment of the stereochemistry of crispatenine
Bourdron, Julien,Commeiras, Laurent,Audran, Gerard,Vanthuyne, Nicolas,Hubaud,Parrain, Jean-Luc
, p. 3770 - 3775 (2008/02/04)
(Figure Presented) The first racemic and enantioselective synthesis of crispatenine 1 has been achieved, which involved a few steps, enabling the assignment of the absolute and relative configurations.
A simple synthesis of γ-cyclohomocitral
Cruz Almanza,Hinojosa Reyes
, p. 867 - 874 (2007/10/02)
A simple and efficient synthesis for γ-cyclohomocitral (10), a key and versatile intermediate for the synthesis of some furanosesquiterpenes, is described. The formal total synthesis of (±) Pallenscensone (2) was accomplished.
Stereoselective Synthesis of (+/-)-Ancistrofuran and its Stereoisomers
Baker, Raymond,Cottrell, Ian F.,Ravenscroft, Paul D.,Swain, Christopher J.
, p. 2463 - 2468 (2007/10/02)
The four possible stereoisomers of ancistrofuran have been prepared from γ-cyclohomocitral.Addition of 3-furyl-lithium yielded two epimeric alcohols.Each alcohol was epoxidised with m-chloroperbenzoic acid and reduction with lithium aluminium hydride gave
New Synthesis of γ-Homocyclogeranial, γ-Dihydroionone and Their Derivatives
Kawanobe, Tsuneo,Kogami, Kunio,Hayashi, Kazuo,Matsui, Masanao
, p. 461 - 464 (2007/10/02)
A new and efficient synthesis of γ-homocyclogeranial (4), γ-dihydroionone (3) and their derivatives, 5, 6, 7 and 8, volatile components of ambergris, is described.Their compounds were synthesized via Claisen rearrangement of (3,3-dimethylcyclohexenyl)methyl vinyl ether (14).
Sulphone-based Elimination Reactions in Synthesis. Part 2. Diumycinol
Kocienski, Philip,Todd, Michael
, p. 1783 - 1789 (2007/10/02)
Diumycinol , a hydrolytic product of the antibiotic diumycin, was assembled from three fragments: 1-(2-phenylsulphonylethyl)-2-methylene-6,6-dimethylcyc
Synthesis of trans-γ-Monocyclofarnesol
Vig, O. P.,Sharma, M. L.,Trehan, Navneet,Verma, N. K.
, p. 450 - 452 (2007/10/02)
The starting material, 2-formyl-6,6,dimethylcyclohexanone (II) in the synthesis of the title compound, is converted into the corresponding 2-isobutoxymethylene-6,6-dimethylcylohexanone (III).Reduction of (III) with LAH followed by treatment with 50percent sulphuric acid gives the α,β-unsaturated aldehyde (IV).LAH reduction of IV yields 1-hydroxymethyl-3,3-dimethylcylohex-1-ene (V) which on mercuric acetate catalysed transetherification with ethyl vinyl ether affords the vinyl ether (VI).Claisen rearragement of VI under an inert atmosphere furnishes 2-(6',6'-dimethyl-2'-methylenecylohexyl)ethanal (VII).Aldehyd VII on Wittig reaction with methoxymethylenetriphenylphosphorane provides the ether (VIII) which is readily converted into the ketal (IX) on treatment with ethylene glycol in the presence of catalytic amount of PTS in dry benzene.Deketalisation of IX with PTS in aq. acetone gives the aldehyde (X) which on Grignard reaction with methylmagnesium iodide furnishes 4-(6',6'-dimethyl-2'-methylenecylohexyl)butan-2-ol (XI).Oxidation of XI with pyridinium chlorochromate in anhydrous methylene chloride yields the ketone (XII) which when subjected to Grignard reaction with vinylmagnesium bromide in dry THF provides the vinylic alcohol (XIII).Treatment of XIII with acetic anhydride and glacical acetic acid in the presence of PTS furnishes the allylic acetate (XIV) which on refluxing with methanolic potassium hydroxide in the presence of a little water gives trans-γ-monocyclofarnesol (I).
