1053733-44-0

Upstream product

• 185670-18-2 (2S,3S,6R)-6-[(2S,3S,6R,8S,9R)-3,9-Dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-3-hydroxy-2-methyl-heptanoic acid methoxy-methyl-amide 
• 185670-27-3 (Z)-(R)-3-Benzyloxycarbonyl-2-methyl-4-triethylsilanyloxy-hex-2-enedioic acid 1-benzyl ester 6-{(R)-1-[(R)-methoxy-(methoxy-methyl-carbamoyl)-methyl]-2-methyl-propyl} ester 
• 185670-22-8 (Z)-2-Methyl-3-((E)-pent-3-enoyl)-but-2-enedioic acid dibenzyl ester 
• 37976-44-6 dibenzylacetylene dicarboxylate 
• 185670-19-3 (3S,4S,7R)-7-[(2S,3S,6R,8S,9R)-3,9-Dimethyl-8-((S)-3-methyl-pent-4-enyl)-1,7-dioxa-spiro[5.5]undec-2-yl]-4-hydroxy-3-methyl-octan-2-one 
• 185670-28-4 (Z)-(R)-3-Benzyloxycarbonyl-2-methyl-4-triethylsilanyloxy-hex-2-enedioic acid 1-benzyl ester 6-((1R,2R)-1-isopropyl-2-methoxy-3-oxo-propyl) ester 

Downstream Products

• 109946-35-2 tautomycin 
• 1054656-75-5 C₅₅H₈₀O₁₄ 

Relevant academic research and scientific papers

Total synthesis of the serine/threonine-specific protein phosphatase inhibitor tautomycin

A convergent, asymmetric synthesis of the protein phosphatase inhibitor, tautomycin, is described. The natural product was constructed by joining two major fragments of comparable complexity at the C21-C22 bond. Absolute stereochemistry of the C1-C21 ketone originates from (S)-citronellene and (2R,3S)-geraniol epoxide. The anti stereochemical relationships at C6-C7 and C18-C19 were introduced with Duthaler's chiral titanium propionic enolate. Syn stereochemical relationships at C13-C14 and C23-C24 were established using an Evan's oxazolidinone chiral auxiliary. The spiroketal was efficiently constructed via a one-pot double-alkylation-spirocyclization sequence with acetone N,N-dimethylhydrazone serving as the central linchpin. Final coupling of the two halves using a chelation-controlled Mukaiyama aldol addition followed by deprotection yielded synthetic tautomycin that is identical to the natural product.