189328-23-2

Upstream product

• 536-74-3 phenylacetylene 
• 171622-74-5 (2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol 
• 197219-77-5 (3S,4S,5R)-4,5-Bis-benzyloxy-3,6-dihydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester 
• 999-90-6 S-tert-butyl thioacetate 
• 189328-22-1 (3S,4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-phenylethynyl-hexanethioic acid S-tert-butyl ester 
• 189328-21-0 (4S,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-one 
• 197219-76-4 (4R,5R)-4,5-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-hex-1-yn-3-ol 
• 162630-99-1 (2S,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butanal 

Downstream Products

• 189328-24-3 3,4-bis(benzyloxy)-1,7-dioxaspiro[4.4]nonan-8-one 
• 197219-86-6 [(2R,3S,4R)-3,4-Bis-benzyloxy-2-((Z)-styryl)-tetrahydro-furan-2-yl]-thioacetic acid S-tert-butyl ester 

Relevant academic research and scientific papers

Total Syntheses of (+)-Secosyrins 1 and 2 and (+)-Syributins 1 and 2

First total syntheses of (+)-secosyrins 1 and 2 and total syntheses of (+)-syributins 1 and 2 are described. The two chiral centers of diisopropyl tartrate were incorporated into target natural products. Stereoselective construction of the spiro skeleton of secosyrins could be realized by taking advantage of an alkyne-cobalt complex. The synthesis of these compounds established their relative and absolute stereochemistry unambiguously.

First total synthesis of (+)-secosyrin 1

The first total synthesis of (+)-secosyrin 1, isolated from P. syringae, pv. tomato, was accomplished in a stereoselective manner from diisopropyl D-tartrate. This synthesis unambiguously established the stereochemistry of (+)-secosyrin 1.