63134-81-6Relevant articles and documents
Exaltone (=Cyclopentadecanone) from Isomuscone (=Cyclohexadecanone), a one-C-atom ring-contraction methodology via a stereospecific favorskii rearrangement: Regioselective application to (-)-(R)-muscone
Chapuis, Christian,Robvieux, Fabrice,Cantatore, Carole,Saint-Leger, Christine,Maggi, Laurent
, p. 428 - 447 (2012/05/07)
Treatment of cyclohexadecanone (1g; with I2 (2.2 mol-euqiv.) and KOH in MeOH) furnished the unsaturated (Z)-ester 2g in 83% yield, via a stereospecific Favorskii rearrangement (Scheme 1). Further treatment with 3-chloroperbenzoic acid (m-CPBA) afforded the unreported epoxy ester 3g (88% yield), which was cleaved in 33% yield to Exaltone (=cyclopentadecanone; 1f) with NaOH in MeOH/H2O and then HCl at 65°. This methodology was similarly extended to higher (C17) and lower (C15 to C11) cyclic ketone analogues, as well as regioselectively to (-)-(R)-muscone (5c) and homomuscone (5f) (Scheme 2). Olfactive properties of the corresponding macrocyclic 1-oxaspiro[2,n]alkanes and -alkenes 4 and 8, resulting from a Coreyi-Chaykovsky oxiranylation, are also presented. Copyright
PREPARATION OF MEDIUM- AND LARGE-SIZED CARBOCYCLES BY MEANS OF SmI2-PROMOTED INTRAMOLECULAR REFORMATSKY REACTION
Inanaga, Junji,Yokoyama, Yasuo,Handa, Yuichi,Yamaguchi, Masaru
, p. 6371 - 6374 (2007/10/02)
Medium- as well as large-sized carbocyclic compounds whose ring skeletons are composed entirely of sp3 carbons have been prepared in high yields under mild conditions by utilizing SmI2-promoted intramolecular Reformatsky reaction.
