182193-69-7

Upstream product

• 105-13-5 4-Methoxybenzyl alcohol 
• 132969-60-9 (2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal 
• 2386-64-3 ethylmagnesium chloride 
• 185203-71-8 methyl (S)-N-methyl-N-methoxy-3-(4-methoxybenzyloxy)-2-methylpropanoate 
• 132969-71-2 methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 307492-62-2 (E)-(2S,4R,5S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-7-phenyl-hept-6-en-3-one 
• 383187-60-8 (1R,2S,4S)-1-Hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-1-(2,3,5-trimethoxy-4-methyl-phenyl)-pentan-3-one 
• 214836-81-4 (E)-(2S,4S,5R)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4,6-trimethyl-7-(2-methyl-oxazol-4-yl)-hept-6-en-3-one 
• 548437-25-8 (2S,4S,5S,6S)-5-hydroxy-1-(p-methoxybenzyloxy)-7-triisopropyloxy-2,4,6-trimethylheptan-3-one 
• 496035-35-9 (2S,4S)-1-hydroxy-5-(p-methoxybenzyloxy)-2,4-dimethylpentan-3-one 
• 827017-68-5 (2S,3R,4S,5S)-1-(4-methoxybenzyloxy)-7-(benzyloxy)-2,4-dimethylheptane-3,5-diol 
• 858948-03-5 (2S,3R,4S,5S)-7-(t-butyldimethylsilyloxy)-1-(4-methoxybenzyloxy)-2,4-dimethyl-heptane-3,5-diol 
• 1036753-09-9 C₂₄H₄₂O₅Si 
• 1184762-47-7 (2S,4S,5R,6S)-6-(tert-butyldimethylsilanyloxymethyl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4,6,10-tetramethylundec-9-en-3-one 
• 1186618-97-2 C₂₄H₄₂O₅Si 
• 1186619-08-8 C₃₄H₄₆O₅Si 
• 1256633-54-1 (2S,4S,5S,7R)-7-(tert-butyldimethylsilyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4-dimethyloctan-3-one 

Relevant academic research and scientific papers

Total synthesis of phorboxazole A via de novo oxazole formation: Strategy and component assembly

The phorboxazole natural products are among the most potent inhibitors of cancer cell division, but they are essentially unavailable from natural sources at present. Laboratory syntheses based upon tri-component fragment coupling strategies have been developed that provide phorboxazole A and analogues in a reliable manner and with unprecedented efficiency. This has been orchestrated to occur via the sequential or simultaneous formation of both of the natural product's oxazole moieties from two serine-derived amides, involving oxidation-cyclodehydrations. The optimized preparation of three pre-assembled components, representing carbons 3-17, 18-30, and 31-46, has been developed. This article details the design and syntheses of these three essential building blocks. The convergent coupling approach is designed to facilitate the incorporation of structural changes within each component to generate unnatural analogues, targeting those with enhanced therapeutic potential and efficacy.

Total synthesis of (-)-basiliskamide B

The total synthesis of the polyketide antibiotic (-)-basiliskamide B is described. The convergent asymmetric synthesis relies on the use of a diastereoselective ethyl ketone aldol reaction followed by a syn selective reduction of a β-hydroxy ketone and a

SYNTHESIS OF DISCODERMOLIDE

The invention relates to a process for preparing discodermolide, for preparing intermediates for the manufacture of discodermolide and discodermolide analogues and to the intermediates obtained during the process. Wherein the process proceeds via a tetrae

Toward the combinatorial synthesis of polyketide libraries: Asymmetric aldol reactions with α-chiral aldehydes on solid support

(Matrix presented) The viability of performing stereocontrolled aldol additions with α-chiral aldehydes attached by a silyl linker to a hydroxymethylpolystyrene resin is demonstrated for boron and titanium enolates. Subsequent ketone reduction and manipul

A convergent three-component total synthesis of the powerful immunosuppressant (-)-sanglifehrin A

The potent immunosuppressive agent (-)-sanglifehrin A (5), initially discovered in a soil sample from Malawi, has been synthesized in a highly conver soil gent and stereocontrolled manner. The enantioselective approach relies on initial construction of th

A practical synthesis of (+)-discodermolide and analogues: Fragment union by complex aldol reactions

A practical stereocontrolled synthesis of (+)-discodermolide (1) has been completed in 10.3% overall yield (23 steps longest linear sequence). The absolute stereochemistry of the C1-C6 (7), C9-C16 (8), and Csub

Stereoselective synthesis of the C(1)-C(12) fragments of tedanolides - Application of a syn-selective tin(II)-mediated aldol reaction and a convertible methoxybenzyl protecting group

Stereoselective synthesis of two C(1)-C(12) fragments, 3 and 4, of antitumor agents tedanolide (1) and 13-deoxytedanolide (2) was achieved by means of several regio- and/or stereoselective reactions. Ethyl ketone 14 was synthesized from methyl (S)-3-hydro

Total synthesis of (+)-crocacin C.

The first asymmetric synthesis of (+)-crocacin C (3) is described which served to confirm the absolute configuration of this compound. The key step in the sequence was the stereoselective assembly of the (E,E)-diene amide side chain by a Stille cross-coup

Synthesis of the central C18-C30 core of the phorboxazole natural products

A direct synthesis of the central C18-C30 core of the phorboxazole natural products has been developed. This involves construction of an acyclic acrylate using Paterson's (E)-enol borinate aldol methodology followed by an intramolecular hetero-Michael addition to form the central pyran ring of the natural products.