59780-28-8Relevant academic research and scientific papers
A highly stereoselective route to medium-ring-sized trans-alkenolides via oxidative fragmentation of bicyclic oxycyclopropane precursors: Application to the synthesis of (+)-recifeiolide
Zubrytski, Dzmitry M.,Kananovich, Dzmitry G.,Kulinkovich, Oleg G.
, p. 2944 - 2950 (2014/04/17)
A new approach to the synthesis of medium-ring-sized trans-alkenolides, based on the oxidative fragmentation of a three-carbon ring in hydroxyalkyl substituted bicyclo[n.1.0]alkan-1-ols readily available from 2-alkylidenecycloalkanones, is described. This methodology was applied to the six-step transformation of cyclooctanone to the natural 12-membered trans-alkenolide antibiotic (+)-recifeiolide.
An efficient synthesis of (R)-(+)-recifeiolide and related macrolides by using enantiomerically pure (R)-(-)-5-methyl-2,2,2-triphenyl-l,2λ5- oxaphospholane
Okuma, Kentaro,Hirabayashi, Syun-ichi,Ono, Masaaki,Shioji, Kosei,Matsuyama, Haruo,Bestmann, Hans J.
, p. 4243 - 4250 (2007/10/03)
E-(R)-(+)-8-Dodece- 11-olide, which is known as recifeiolide, was synthesized by a six-step reaction starting from (R)-(+)-propene oxide in a total yield of 53 %. The key step of this synthesis is the preparation of (R)-(-)-methyl 11-hydroxy-8-dodecenate using (R)-(-)-5-methyl-2,2,2- triphenyl-1,2λ5-oxaphospholane. By using this method, enantiomerically pure 13- and 14-membered macrolides were also synthesized.
Stereospecific annulation of hydroxy vinyl ethers. Synthetic application to polyfunctionalized cyclic compounds
Hanaki, Naoyuki,Ishihara, Kazuaki,Kaino, Makoto,Naruse, Yuji,Yamamoto, Hisashi
, p. 7297 - 7320 (2007/10/03)
Stereospecific annulation of hydroxy vinyl ethers in the presence of triflic anhydride and tertiary amines and its synthetic application are described. Each 1-hydroxy-2-oxabicyclo(n.4.0)alkane, 2-oxabicyclo(n.4.0)alk-1(6)-ene and 2-oxabicyclo(n.4.0)alk-1(6+n)-ene is stereoselectivity synthesized from the same hydroxy vinyl ether depending on the choice of the reaction conditions (temperature, solvent and tertiary amine). These compounds lead to polyfunctionalized cyclic compounds and some natural product. We propose that this annulation reaction proceeds through a pure S(N)2-like mechanism.
Stereospecific Cyclization of Vinyl Ether Alcohols. Facile Synthesis of (-)-Lardolure
Kaino, Makoto,Naruse, Yuji,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 5814 - 5815 (2007/10/02)
An efficient and stereospecific ring formation from unsaturated alcohols, which in turn are prepared by regio- and stereospecific ring opening of acetals, is described.
