306281-52-7

Upstream product

• 208338-27-6 tert-Butyl-[(R)-1-((R)-1-methyl-2-phenyl-ethyl)-4-(1-oxo-1λ⁴-[1,3]dithian-2-yl)-butoxy]-diphenyl-silane 
• 172790-39-5 (2R,3R,4S,5S)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-ol 
• 306281-45-8 (2Z,4E)-ethyl 6-benzyloxy-3,4-bis(benzyloxymethyl)-2,4-hexadienoate 
• 172790-31-7 (2E,4Z)-6-benzyloxy-3,4-bis(benzyloxymethyl)-2,4-hexadienol 
• 306281-44-7 (Z)-ethyl 4-(benzyloxy)-3-iodo-2-butenoate 
• 172790-40-8 (2S,3R,4S,5R)-2,3,4,5-bis(di-O-isopropylidene)-6-benzyloxy-(3,4-bis(benzyloxymethyl))hexan-1-al 
• 208338-40-3 (5R,6R)-O-benzyl-5-(tert-butyldiphenylsilyloxy)-6-methyl-7-phenylheptan-1-ol 
• 208338-26-5 (4'R,5'R)-2-[4'-(tert-butyldiphenylsilyloxy)-5'-methyl-6'-phenylhex-1'-yl][1,3]dithiane 
• 306281-48-1 (5R,6R)-5-(tert-butyldiphenylsilyloxy)-6-methyl-7-phenylheptan-1-ol 
• 306281-49-2 (5R,6R)-5-(tert-butyldiphenylsilyloxy)-6-methyl-7-phenylheptanal 
• 171189-83-6 (2R,3R)-7-Benzyloxy-2-methyl-1-phenyl-heptan-3-ol 
• 138435-42-4 4-benzyloxybut-2-ynoic acid ethyl ester 
• 4039-82-1 Benzyl propargyl ether 
• 108-24-7 acetic anhydride 

Downstream Products

• 208338-37-8 (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(benzyloxymethyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane 

Relevant academic research and scientific papers

Total Synthesis of (+)-Zaragozic Acid C

A total synthesis of (+)-zaragozic acid C is described. Key features of the synthesis are the use of a double Sharpless asymmetric dihydroxylation reaction of diene 6 to control stereochemistry at four contiguous stereocenters from C3 to C6; the introduction of the C1-side chain by reaction between the anion derived from the dithiane monosulfoxide 27 and the core aldehyde 12; a high yielding, acid-mediated simultaneous acetonide deprotection-dithiane removal-ketalization procedure leading exclusively to the 2,8-dioxabicyclo[3.2.1]octane core 34; and a novel triple oxidation procedure allowing installation of the tricarboxylic acid.