35433-73-9Relevant academic research and scientific papers
Catalytic enantioselective synthesis of macrolides via asymmetric alkylation
Jones, Graham B.,Huber, Robert S.,Chapman, Brant J.
, p. 1797 - 1809 (2007/10/03)
Catalytic enantioselective syntheses of the macrolides (R)-(-) phoracantholide and (R)-(+) lasiodiplodin have been achieved. Stereochemistry was introduced in using an arene chromium tricarbonyl derived catalyst, which mediated the enantioselective additi
Insect pheromone synthesis using Mn-salen catalyzed asymmetric epoxidation as a key step
Hamada,Daikai,Irie,Katsuki
, p. 2441 - 2451 (2007/10/03)
Enantioselective synthesis of three insect pheromones, (5Z, 13S)-5-tetradecen-13-olide, (9R)-decan-9-olide, and (S)-2-acetoxytridecane, has been achieved by using Mn-salen catalyzed asymmetric epoxidation as a key step.
Synthesis of Both the Enantiomers of Phoracantholide I; A Defensive Secretion of the Eucarypt Longicorn (Phoracantha synonyma), Employing Microbial Asymmetric Reduction with Immobilized Baker's Yeast
Naoshima, Yoshinobu,Hasegawa, Hidenobu,Nishiyama, Tadashi,Nakamura, Akihiro
, p. 608 - 610 (2007/10/02)
Highly optically pure (R)- and (S)-phoracantholide I were synthesized in relatively short steps starting from diethyl 3-oxoglutarate by means of a microbial asymmetric reduction of the intermediate keto acid with immobilized baker's yeast entrapped in gels of κ-carrageenan.
Synthesis of Both Enantiomers of Phoracantholide I, a Defensive Secretion of the Eucarypt Longicorn, Employing Asymmetric Reduction with Immobilized Baker's Yeast
Naoshima, Yoshinobu,Hasegawa, Hidenobu
, p. 2379 - 2382 (2007/10/02)
Highly enantiomerically pure (R)- and (S)-phoracantholide I were synthesized in relatively short steps starting from diethyl 3-oxoglutarate by means of an asymmetric reduction of the intermediate keto acid with immobilized baker's yeast.The asymmetric reduction with the immobilized baker's yeast gave greater facilities compared with the analogous reaction with free baker's yeast.
Orthocarbonsaeure-ester mit 2,4,10-Trioxaadamantanstruktur als Carboxylschutzgruppe; Verwendung zur Synthese von substituierten Carbonsaeuren mit Hilfe von Grignard-Reagenzien
Voss, Gundula,Gerlach, Hans
, p. 2294 - 2307 (2007/10/02)
The surprising stability of 2,4,10-trioxa-3-adamantyl derivatives 1 against nucleophilic substitution by organomagnesium compounds is discussed and shown to be caused by unfavourable stereoelectronic and steric factors governing the substitution of these cage compounds (Scheme 2).As a consequence, a number of Grignard reagents 2 containing the carboxyl group masked as 2,4,10-trioxa-3-adamantyl group could be prepared and have been reacted in a second step with various electrophiles (cf.Scheme 4).In the products 7-13 and 15b the carboxyl masking group is removed by mild ac id hydrolysis and saponification (cf.Scheme 3) to yield the corresponding acids 16a-21a, 22, and 23a.Acids 21a and 23a have been further transformed to give the macrocyclic lactones 24 and 26, isolated from Galbanum oleo-gum-resin, and acid 22 to give 12-methyl-13-tridecanolide (25), isolated from Angelica root oil.In addition 1-bromo-ω-(2,4,10-trioxa-3-adamantyl)alkanes 1c and 1b have been used to synthesize (+/-)-methyl recifeiolate (29b) and pure cis-ambrettolic acid ((Z)-32a).
2,3-Alkadiensaeureester als Dienophile; Anwendung bei der Synthese von (+)-(R)-Lasiodiplodin
Fink, Margot,Gaier, Hans,Gerlach, Hans
, p. 2563 - 2569 (2007/10/02)
Methyl 2,3-alkadienoates 2 are shown to react at 80 deg C with 1,1-dimethoxy-3-trimethylsilyloxy-1,3-butadiene (1) to give the adducts 3 in good yields.Rearrangement of 3, catalyzed by p-toluenesulfonic acid or by sodium methoxide, affords the 6-substitut
