1903-26-0Relevant articles and documents
Claisen rearrangement based methodology for the spiroannulation of a cyclopentane ring. Formal total synthesis of (±)-acorone and isoacorones
Srikrishna,Praveen Kumar
, p. 8189 - 8195 (2007/10/03)
A Claisen rearrangement based methodology for spiroannulation of a cyclopentane ring to cyclic precursors and its application in the formal total synthesis of acorones 1 is described. Thus, Claisen rearrangement of 2-cycloalkylideneethanols 12 with 2-methoxypropene and a catalytic amount of mercuric acetate generates 4,4-substituted hex-5-en-2-ones 13. Ozonolytic cleavage of the terminal olefin in the enones 13 and intramolecular aldol condensation of the resulting keto-aldehydes 14 furnishes the spiroannulated compounds 15. (C) 2000 Elsevier Science Ltd.
Spiroannulation of a cyclopentane ring. Synthesis of spiro[4.n](n+5)alk-2-en-1-ones
Srikrishna,Kumar, P. Praveen
, p. 521 - 526 (2007/10/03)
A methodology based on Claisen rearrangement-Wacker oxidation and intramolecular aldol condensation strategy starting from cyclic ketones leading to spiro[4.n](n+5)alk-2-en-1-ones has been developed. Thus one-pot Claisen rearrangement of the allyl alcohols 6a-c furnished the aldehydes 8a-c, which on regiospecific oxidation using Wacker conditions generated the keto-aldehydes 9a-c. Finally, intramolecular aldol condensation transformed the keto-aldehydes 9a-c into spiroannulated products 10a-c.
A simple strategy for spirocyclopentannulation of cyclic ketones. Formal total synthesis of (±)-acorone
Srikrishna, Adusumilli,Kumar, P. Praveen,Viswajanani, Ranganathan
, p. 1683 - 1686 (2007/10/03)
A general and simple methodology for spirocyclopentannulation of cyclic ketones (or 4,4-disubstituted cyclopentenones from acyclic ketones) and its application in the synthesis of the spirodienone 7 via a prochiral precursor constituting a formal total synthesis of (±)-acorone (6), are described.
Synthesis and antiallergy activity of [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives. II. 6-Alkyl- and 6-cycloalkylalkyl derivatives
Yokohama,Miwa,Aibara,Fujiwara,Matsumoto,Nakayama,Iwamoto,Mori,Moroi,Tsukada,Isoda
, p. 2391 - 2398 (2007/10/02)
A series of 6-alkyl- or 6-(cycloalkylalkyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyr imidin-9(3H)-ones 1b-o was synthesized from the corresponding 1,3,4-thiadiazol-5-amines 3b-o and the antiallergic activities of the products were evaluated. Among the compounds 6-(2-cyclohexylethyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]p yrimidin-9(3H)-one 1h, whose X-ray crystallographic stereostructure is shown, was found to be a promising new antiallergic agent, which has low toxicity and dual activity as a leukotriene D4 receptor antagonist and as an orally active mast cell stabilizer.
STNTHESIS OF 13-OXABICYCLOPENTADECANE FROM CYCLODODECANONE
Zakharkin, L. I.,Churilova, I. M.,Ovseenko, S. T.
, p. 1696 - 1699 (2007/10/02)
A simple method was developed for the synthesis of 12-oxabicyclopentadecane from cyclododecanone through α-allylcyclododecanone .A mixture of cyclododecenylacetc and cyclododecenylideneacetic acids, the nitriles of these acids, and their ethyl esters was obtained from cyclododecanone, and the composition of the equilibrium mixture of compounds was established by means of the PMR spectra. 14-Oxo-13-oxabicyclopentadecane was obtained by the cyclization of cyclododecenylacetic acid and the cyclization of 2-hydroxycyclododecylacetic acid