296795-36-3

Upstream product

• 296795-14-7 1-((7S,9R)-9-(benzyloxymethyl)-1,4,8-trioxaspiro[4.5]dec-7-yl)-propan-2-one 
• 296795-17-0 9(R)-9-(benzyloxymethyl)-1,4,8-trioxaspiro[4.5]dec-7-yl acetate 
• 310883-71-7 (4R)-4-benzyl-3-[(3R)-3-(triethylsilyloxy)-3-(2-(triisopropylsilyloxymethyl)-1,3-oxazol-4-yl)propanoyl]-2-oxazolidinone 
• 310883-72-8 (3R)-3-(triethylsilyloxy)-3-(2-(triisopropylsilyloxymethyl)-1,3-oxazol-4-yl)-propanol 
• 1027560-84-4 3-[2-(1,2-dihydroxy-2-phenyl-ethyl)-oxazol-4-yl]-3-triethylsilanyloxy-thiopropionic acid S-tert-butyl ester 
• 296795-34-1 (3R)-3-(2-((E)-2-phenyl-1-etheny)-1,3-oxazol-4-yl)-3-(triethylsilyloxy)thiopropionic acid S-tert-butyl ester 
• 259809-67-1 2-[(E)-2-phenylethenyl]oxazole-4-carbaldehyde 
• 132629-37-9 ethyl 2-[(E)-2-phenylethenyl]oxazole-4-carboxylate 
• 80522-42-5 triisopropylsilyl trifluoromethanesulfonate 
• 994-30-9 triethylsilyl chloride 
• 296795-20-5 (4R,6R)-1-((7S,9R)-9-(benzyloxymethyl)-1,4,8-trioxa-spiro[4.5]dec-7-yl)-4-hydroxy-6-(triethylsilyloxy)-6-(2-(triisopropylsilyloxymethyl)-1,3-oxazol-4-yl)-hexan-2-one 
• 310883-69-3 (4R)-4-benzyl-3-[(2R,3S)-2-chloro-3-hydroxy-3-(2-(triisopropylsilyloxymethyl)-1,3-oxazol-4-yl)propanoyl]-2-oxazolidinone 
• 310883-70-6 (4R)-4-benzyl-3-[(3R)-3-hydroxy-3-(2-(triisopropylsilyloxymethyl)-1,3-oxazole-4-yl)propanoyl]-2-oxazolidinone 
• 181633-67-0 ethyl 2-hydroxymethyl-oxazole-4-carboxylate 

Downstream Products

• 296795-41-0 (2R,6S)-2-(benzyloxymethyl)-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(triisopropylsilyloxy)methyl-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)-methyl)-tetrahydro-4H-pyran-4-one 
• 296795-25-0 N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide 
• 296795-21-6 4-((2R,4S,6R)-6-(((7S,9R)-9-(benzyloxymethyl)-1,4,8-trioxaspiro-[4.5]dec-7-yl)methyl)-4-(triisopropylsilyloxy)tetrahydro-2H-pyran-2-yl)-2-(triisopropylsilyloxymethyl)-1,3-oxazole 
• 296795-24-9 N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(triisopropyloxy)methyl-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-yn-amide 
• 296795-37-4 N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(hydroxymethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide 
• 296795-13-6 4-((2R,4R,6R)-6-(((7S,9R)-9-(benzyloxymethyl)-1,4,8-trioxaspiro[4.5]dec-7-yl)methyl)-6-hydroxy-4-(triisopropylsilyloxy)tetrahydro-2H-pyran-2-yl)-2-(triisopropylsilyloxymethyl)-1,3-oxazole 

Relevant academic research and scientific papers

Application of complex aldol reactions to the total synthesis of phorboxazole B

The synthesis of phorboxazole B has been accomplished in 27 linear steps and an overall yield of 12.6%. The absolute stereochemistry of the C4-C12, C33-C38, and C13-C19 fragments was established utilizing catalytic asymmetric aldol methodology, while the absolute stereochemistry of the C20-C32 fragment was derived from an auxiliary-based asymmetric aldol reaction. All remaining chirality was incorporated through internal asymmetric induction, with the exception of the C43 stereocenter which was derived from (R)-trityl glycidol. Key fragment couplings include a stereoselective double stereodifferentiating aldol reaction, a metalated oxazole alkylation, an oxazole-stabilized Wittig olefination, and a chelation-controlled addition of the fully elaborated alkenyl metal side chain.