126550-68-3Relevant academic research and scientific papers
Stereocontrolled synthesis of the tetrahydrofuran unit of annonaceous acetogenins
Li, Keqiang,Vig, Shikha,Uckun, Fatih M.
, p. 2063 - 2066 (1998)
The THF-epoxide 8 has been prepared from benzyl (R)-(-)-glycidyl ether using a 10-step synthetic scheme in a stereocontrolled fashion. Compound 8 is a highly useful synthon for the synthesis of mono- and di-THF acetogenins. This new synthetic approach can
First total synthesis of Debilisone C
Saikia, Bishwajit,Joymati Devi, Thongam,Barua, Nabin C.
, p. 905 - 913 (2013/03/14)
Total synthesis of Debilisone C, a lactone containing conjugated endiyne has been achieved. The adopted strategy involves the stereoselective construction of the five membered lactone ring and the C20 endiyne chain followed by regioselective coupling of both the parts. The lactone was obtained from the oxidative cleavage of the hydroxy olefin which was derived from the benzyl protected S-epichlorohydrine by regioselective epoxide opening with allyl trimethyl silane in presence of a Lewis acid at -78 °C. Takai olefination, Pd0/Ag1 catalyzed cross-coupling reaction and selective substitution of trimethylsilyl groups were successfully utilized to establish the C20 polyyne chain. The final coupling of both the parts have been carried out by alkyl coupling using LDA in THF-DMPU (1 : 1).
NHC-catalyzed ring expansion of oxacycloalkane-2-carboxaldehydes: A versatile synthesis of lactones
Wang, Li,Thai, Karen,Gravel, Michel
supporting information; experimental part, p. 891 - 893 (2009/08/15)
Imidazolinium-derived carbenes catalyze the ring-expansion lactonization of oxacycloalkane-2-carboxaldehydes. A variety of functionalized five-, six-, and seven-membered lactones can be formed efficiently under mild reaction conditions. The success of this new method for the construction of lactones is highly influenced by the electronic nature of the carbene catalyst.
Stereoselective Synthesis of Aliphatic 1,5,9,13-Polyols using (δ-Alkoxyallyl)stannanes
McNeill, Alan H.,Thomas, Eric J.
, p. 1669 - 1672 (2007/10/02)
Treatment of aliphatic aldehydes with the allyltin trichloride generated from the 4-benzyloxyocta-2,7-dienylstannane 18 and tin(IV)chloride provides stereoselective access to polyhydroxylated compounds with the hydroxyl groups at positions 1,5,9,13- etc.
A Convenient Synthesis of (R)-Japonilure
Chattopadhyay, S.,Mamdapur, V. R.,Chadha, M. S.
, p. 1299 - 1303 (2007/10/02)
The title pheromone has been synthesised in high optical purity using easily accessible (S)-glycerol-2,3-acetonide (2) as the starting chiron.
