530112-01-7

Upstream product

• 67-56-1 methanol 
• 529488-03-7 2,6-anhydro-1-O-[tert-butyl(dimethyl)silyl]-4-O-[tert-butyl-(diphenyl)silyl]-3,5-dideoxy-D-threo-hex-5-enitol 

Downstream Products

• 529488-04-8 Trifluoro-methanesulfonic acid (2S,4S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester 
• 529488-16-2 2-(acetyloxy)-6-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}benzoic acid 
• 529488-09-3 {(2S,4S,6R)-2-allyl-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane 
• 529488-11-7 3-{(2R,4S)-4-[tert-butyl(diphenyl)silyloxy]-6-methoxytetrahydro-2H-pyran-2-ylmethyl}-2-formylphenyl acetate 
• 529488-06-0 {(4S,6R)-2-methoxy-6-[(2-methyl-1-benzofuran-4-yl)methyl]-tetrahydro-2H-pyran-4-yloxy}(tert-butyl)diphenylsilane 

Relevant academic research and scientific papers

A formal total synthesis of (+)-apicularen A: Base-induced conversion of apicularen-derived intermediates into salicylihalamide-like products

A synthesis of apicularen precursor (-)-6 in 18 steps from D-glucal is reported. As (+)-6 has been converted into the potent, naturally occurring salicylate anti-cancer agent, (-)-apicularen A in 8 steps, this study constitutes a formal total synthesis of (+)-apicularen A. Key steps in the synthetic route include: (i) useful D-glucal elaboration processes. (ii) organometallic displacements at carbohydrate C-6 triflates using Knochel-type and related functionalised, aromatic Grignard reagents, (iii) stereoselective allyltrimethylsilane-acetal reactions generating C-allyl systems. (iv) stereocontrolled aldehyde allylation processes from both substrate and reagent, and (v) a novel Keck-type macrolactonisation. In addition, preliminary studies are reported in which a procedure has been devised to convert apicularen-derived intermediates into salicylihalamide-like products.