35433-72-8Relevant articles and documents
Catalytic enantioselective macrolide synthesis II: Use of differential deprotection protocols
Jones,Chapman,Huber,Beaty
, p. 1199 - 1202 (2007/10/02)
Catalytic enantioselective synthesis of Phorcantholide I has been achieved. Key stereochemistry was introduced using a chiral arene chromium tricarbonyl based catalyst to mediate the addition of dimethyl zinc to a functionalised aldehyde. During the synth
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.
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).