10521-08-1Relevant articles and documents
Syntheses of 2-Carbomethoxy-5,10-dimethyl-6,8-bisdehydroannulenone, a Potential Precursor of Macrocyclic Azulene Analogues, and (Z)- and (E)-14-Carbethoxy-2-carbomethoxy-5,10-dimethyl-6,8-bisdehydrofulvenes
Sharma, Vijay K.,Shahriari-Zavareh, Hooshang,Garratt, Peter J.,Sondheimer, Franz
, p. 2379 - 2383 (1983)
The synthesis of 2-carbomethoxy-5,10-dimethyl-6,8-bisdehydroannulenone (15), a potential precursor of macrocyclic azulene analogues, and its elaboration into (E)- (19) and (Z)-14-carbethoxy-2-carbomethoxy-5,10-dimethyl-6,8-bisdehydrofulvene (20) is reported.The 1H NMR spectrum of 15 is interpreted to indicate that in the average conformation the C-12,13 double bond is not coplanar with the ring, and a reappraisal of the conformation of 2,5,10-trimethyl-6,8-bisdehydroannulenone (16b) is made.The fulvenes 19 and 20 show little or no paratropicity and serve as model systems for the estimation of paratropicity in 15 and related systems.
Synthesis of 3-[(tert-Butyldimethylsilyl)oxy]glutaric anhydride from citric acid
Jiang,Wang
, p. 7867 - 7868 (2014)
A new synthesis of 3-[(tert-butyldimethylsilyl)oxy]glutaric anhydride has been developed from citric acid, which is a commodity chemical and more than a million tons are produced every year by fermentation. The new synthetic approach demonstrated an efficient utilization of bioresource for the synthesis of intermediate of rosuvastatin.
Chiral Aryliodine-Mediated Enantioselective Organocatalytic Spirocyclization: Synthesis of Spirofurooxindoles via Cascade Oxidative C-O and C-C Bond Formation
Cao, Yang,Zhang, Xiang,Lin, Guangyu,Zhang-Negrerie, Daisy,Du, Yunfei
supporting information, p. 5580 - 5583 (2016/11/17)
An enantioselective organocatalytic oxidative spirocyclization of alkyl 3-oxopentanedioate monoamide derivatives leading to the formation of diverse spirofurooxindoles with high enantioselectivity has been realized via chiral aryliodine-mediated cascade C-O and C-C bond formations. The reaction is postulated to proceed via oxidative C-O bond formation followed by oxidative C-C bond formation, with the latter being the enantioselectivity-determining step.
An efficient process for the manufacture of carmegliptin
Abrecht, Stefan,Adam, Jean-Michel,Bromberger, Ulrike,Diodone, Ralph,Fettes, Alec,Fischer, Rolf,Goeckel, Volker,Hildbrand, Stefan,Moine, Gerard,Weber, Martin
experimental part, p. 503 - 514 (2012/01/03)
A short and high-yielding synthesis of carmegliptin (1) suitable for large-scale production is reported. The tricyclic core was assembled efficiently by a decarboxylative Mannich addition-Mannich cyclization sequence. Subsequent crystallization-induced dynamic resolution of enamine 7 using (S,S)-dibenzoyltartaric acid was followed by diastereoselective enamine reduction to give the fully functionalized tricyclic core with its three stereogenic centers. The C-3 nitrogen was introduced by Hofmann rearrangement of amide 28, and the resulting amine 10 was coupled with (S)-fluoromethyl lactone 31. Following cyclization to lactam 13 and amine deprotection, 1 was obtained in 27-31% overall yield with six isolated intermediates.
