35433-72-8

Upstream product

• 69008-87-3 2-decen-9-olide (E isomer) 
• 88784-99-0 1-Brom-4-(2,4,10-trioxatricyclo<3.3.1.1^3,7>dec-3-yl)hexan 
• 20965-27-9 7-bromo-heptanonitrile 
• 629-03-8 1 ,6-dibromohexane 
• 157730-85-3 (R)-(+)-9-trityloxy-2-decanol 
• 157730-86-4 1-trityloxy-9-t-butyldimethylsilyloxydecane 
• 157730-87-5 9-t-butyldimethylsilyloxy-1-decanol 
• 157730-88-6 (S)-9-(tert-Butyl-dimethyl-silanyloxy)-decanoic acid 
• 88785-11-9 (+)-(S)-9-(2,4,10-Trioxatricyclo<3.3.1.1^3,7>dec-3-yl)-2-nonanol 
• 1422-26-0 9-oxodecanoic acid 

Downstream Products

• 61448-27-9 (S)-(+)-phoracantholide I 
• 61448-27-9 (R)-(-)-phoracantholide I 

Relevant academic research and scientific papers

Catalytic enantioselective macrolide synthesis II: Use of differential deprotection protocols

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

Enzymatic Resolution of Medium-Ring Lactones. Synthesis of (S)-(+)-Phoracantholide I

The horse liver and pig liver esterase hydrolysis of racemic medium ring lactones gives with excellent enantiomeric excess the S- (or R) lactones and the corresponding R- (or S) hydroxy acids.This is the first general method to obtain optically pure medium ring lactones.Application to the preparation of (S)-(+)-Phoracantholide I is reported.

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

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

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

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).