310883-84-2

Upstream product

• 101712-01-0 (R)-1-((R)-4-benzyl-2-oxooxazolidin-3-yl)-2-methylpentane-1,3-dione 
• 139630-91-4 (E)-2-methyl-3-(2-methyloxazol-4-yl)acrylaldehyde 
• 76-86-8 Triphenylsilyl chloride 
• 310883-82-0 {(2R,3R,4R,5S,6R)-2-Hydroxy-3,5-dimethyl-6-[(E)-1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-4-triphenylsilanyloxy-tetrahydro-pyran-2-yl}-acetic acid tert-butyl ester 
• 310883-81-9 6-[(E)-1-methyl-2-(2-methyl(oxazol-4-yl))vinyl](5S,3R,4R,6R)-3,5-dimethyl-4-(triphenylsilyloxy)-tetrahydro-2H-pyran-2-one 
• 310883-80-8 (E)-3-[(2R,3R,4R,5R)-3,5-dihydroxy-7-(2-methyl(oxazol-4-yl))-1-oxo-2,4,6-trimethyl-6-heptenyl]-(4R)-benzyl-2-oxazolidinone 
• 310883-83-1 tert-butyl 2-{6-[(E)-1-methyl-2-(2-methyl(oxaszol-4-yl))vinyl](3S,4S,2R,5S,6R)-3,5-dimethyl-4-(triphenylsilyloxy)-tetrahydro-2H-pyran-2-yl}acetate 

Downstream Products

• 310883-85-3 2-[(E)-1-methyl-2-(2-methyl(oxazol-4-yl))vinyl](2R,3S,4S,5S,6R)-3,5-dimethyl-6-[2-(trimethylsilyloxy)ethyl]-4-(triphenylsilyloxy)-tetrahydro-2H-pyran 
• 296785-20-1 (2S,4R,6R)-2-[4-((E)-2-[(2R,3S,4S,5S,6R)-3,5-dimethyl-6-(2-trimethylsilyloxyethyl)-4-triphenylsilyloxy-tetrahydro-2H-pyran-2-yl]prop-1-enyl)(1,3-oxazol-2-yl)]methyl-4-methoxy-6-triethylsilyloxymethyl-tetrahydro-2H-pyran-2-ol 
• 310883-88-6 (2R,4R,6R)-2-[4-((E)-2-[(2R,3S,4S,5S,6R)-3,5-dimethyl-6-[2-(trimethylsilyloxyethyl)]-4-(triphenylsilyloxy)-tetrahydro-2H-pyran-2-yl]prop-1-enyl)(1,3-oxazol-2-yl)]-methyl-4-methoxy-2-(triethylsilyloxy)-6-(triethylsilyloxymethyl)-tetrahydro-2H-pyran-2-ol 

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.

Asymmetric synthesis of phorboxazole B - Part I: Synthesis of the C20-C38 and C39-C46 subunits

The total synthesis of the antitumor marine macrolide phorboxazole B (1) has been realized. The phorboxazoles are representative of a new structural class of macrolides and are among the most cytostatic natural products known: inhibiting the growth of tum