477953-48-3

Upstream product

• 624-64-6 trans-2-Butene 
• 115869-43-7 (tert-butyldiphenylsilanyloxy)acetaldehyde 
• 145365-08-8 (Z)-2,2,11,11-tetramethyl-3,3,10,10-tetraphenyl-4,9-dioxa-3,10-disiladodec-6-ene 

Downstream Products

• 477953-56-3 (Z)-(2R,3R,6S,9S)-1-(tert-Butyl-diphenyl-silanyloxy)-10-((2S,6R)-6-iodomethyl-tetrahydro-pyran-2-yl)-9-(4-methoxy-benzyloxy)-3-methyl-dec-4-ene-2,6-diol 
• 477953-61-0 (S)-1-{(2S,5S,7R,8R)-7-[(Z)-(R)-1-Hydroxy-6-(4-methoxy-benzyloxy)-hex-3-enyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-hept-6-en-2-ol 
• 930795-40-7 (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate 
• 930795-43-0 (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-ethynyl-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate 
• 930795-41-8 (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate 
• 930795-42-9 acetic acid 1-[1-(2-cyano-ethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-3-methyl-cyclohex-3-enyl]-5-[3-methyl-5-(3-triisopropylsilanyloxy-propyl)-tetrahydro-furan-2-yl]-hex-4-enyl ester 
• 930795-15-6 diethyl (2'S,4'R,5'R)-2-[(5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl)methyl]malonate 
• 930795-12-3 (3R,4R)-4,5-bis(2,6-dichlorobenzyloxy)-3-methylpentan-1-ol 
• 930795-13-4 (4R,5R)-5,6-bis(2,6-dichlorobenzyloxy)-4-methylhex-1-ene 
• 930795-47-4 (3R,4R)-4,5-bis(2,6-dichlorobenzyloxy)-3-methylpentanal 
• 930795-46-3 (3R,4R)-4,5-bis(2,6-dichlorobenzyloxy)-3-methyl-pent-1-ene 

Relevant academic research and scientific papers

Studies on the synthesis of (-)-gymnodimine. Subunit synthesis and coupling

Two principal subunits of the marine algal toxin (-)-gymnodimine were synthesized. A trisubstituted tetrahydrofuran representing C10-C18 of the toxin was prepared via a highly stereoselective iodine-mediated cyclization of an acyclic alkene bearing a bis-

Silicon tether-aided coupling metathesis: Application to the synthesis of attenol A

(matrixpresented) A new synthesis of attenol A is described. Key features of this work include a crucial silicon tether-aided coupling metathesis step and the use of iodoetherification as an efficient protection method for 1,5-ene-ols.

Total Synthesis of Tautomycin

A convergent stereocontrolled synthesis of the antifungal antibiotic tautomycin, a potent protein phosphatases inhibitor, has been achieved first via key aldol coupling of two large subunits, a right-hand C1-C21 ketone and a left-hand aldehyde (left from C22).The C1-C10 segment was synthesized through a remote stereochemical control process using a spiroketal template.After joining with the C11-C18 segment, the spiroketal moiety was selectively constructed.Then the right-hand C1-C21 ketone was synthesized via Roush asymmetric crotylboration.The left-hand aldehyde was prepared from a C21-C26 segment and a dialkylmaleic anhydride segment.Completely stereoselective assemblage of the two subunits, the right-hand and the left-hand, was achieved by employing the Mukaiyama aldol reaction.Further functional group manipulation including desilylation, oxidation at C2, and deprotection of tert-butyl ester with concomitant anhydride formation provided tautomycin which was identical with the natural product.As a preliminary study, derivatizations and degradation of the natural product were also examined to support the total synthesis.