208586-53-2

Upstream product

• 42890-76-6 (S)-1,2,4-butanetriol 
• 123-11-5 4-methoxy-benzaldehyde 
• 103708-37-8 (2S,4S)-4-hydroxymethyl-2-(p-methoxymethyl)-1,3-dioxane 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 

Downstream Products

• 501084-18-0 (1RS)-1-[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-1-ethanol 
• 1176003-81-8 1-[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-5-methylhex-4-en-2-yn-1-ol 
• 1027785-22-3 (2S,4S)-2-(4-methoxyphenyl)-4-[(E)-4-(tritylthio)but-1-enyl]-1,3-dioxane 
• 208586-46-3 (2S,4S)-4-Ethynyl-2-(4-methoxy-phenyl)-[1,3]dioxane 
• 631416-67-6 (2S,4S)-2-(4-Methoxy-phenyl)-4-vinyl-[1,3]dioxane 
• 501084-20-4 (3S)-3-hydroxy-3-[(2R,4R)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-1-[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-1-propanone 
• 501084-19-1 (3R)-3-hydroxy-3-[(2R,4R)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-1-[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]-1-propanone 
• 501084-22-6 (1S,3R)-1-[(2S,4S)-2-(4-Methoxy-phenyl)-[1,3]dioxan-4-yl]-3-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-propane-1,3-diol 
• 501084-21-5 (1R,3S)-1-[(2S,4S)-2-(4-Methoxy-phenyl)-[1,3]dioxan-4-yl]-3-[(2R,4R)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-propane-1,3-diol 
• 198768-49-9 (-)-1-[(2S,4S)-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]ethanone 

Relevant academic research and scientific papers

Studies towards the total synthesis of (-)-caulerpenynol, a toxic sesquiterpenoid of the green seaweed caulerpa taxifolia

The first diastereoselective synthesis of the antimicrobial and cytotoxic agent (-)-caulerpenynol (2) was achieved in relatively few steps from, commercially available (S)-malic acid, Highlights of this synthesis include the nonracemization. of the sensitive a-hydroxy ketone moiety and the proper choice of the protecting groups for critical last deprotection step. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

Synthesis of 1alpha,25-dihydroxyvitamin D3-26,23-lactams (DLAMs), a novel series of 1 alpha,25-dihydroxyvitamin D3 antagonist.

Novel vitamin D(3) analogs having a lactam structure in their side chains, 1 alpha,25-dihydroxyvitamin D(3)-26,23-lactams (DLAMs), were designed based on the principle of regulation of the folding of helix-12 in the vitamin D nuclear receptor (VDR). The n

Synthesis and conformational analysis of meso-ter(1,3-dioxan-4-yls)

A convergent synthesis of the meso-ter(1,3-dioxanyls) 8-11 has been achieved, starting from two enantiomeric building blocks in each case. The stereogenic centres in the central linkage region were set up by stereocontrolled aldol additions. Structure ass

Asymmetric synthesis of (+)-loline, a pyrrolizidine alkaloid from rye grass and tall fescue

(+)-Loline (1) was synthesized via a pathway that employed intramolecular [4 + 2] cycloaddition of an acylnitrosodiene, 25 or 26, as a key step. The acylnitrosodienes, which were used in situ, were obtained by oxidation of the corresponding hydroxamic acids, 17 and 24, and these were prepared from either glucose via aldehyde 9 or more directly from (S)-malic acid (18). The endo dihydrooxazines 27 and 29, obtained in a mixture with their exo stereoisomer, were transformed by reductive N-O bond cleavage and reannulation into pyrrolizines 34 and 35. The latter was subjected to Sharpless aminohydroxylation in the presence of (DHQD)2PHAL to give 50 along with its regioisomer 51. N-Methylation of tosyl amide 50, followed by mesylation of alcohol 52 and reduction of the γ-lactam 53 with borane, afforded pyrrolizidine 54. Cleavage of the p-methoxybenzyl ether and subsequent thermal treatment of 55 resulted in intramolecular etherification to yield N-tosylloline (57). Final reductive cleavage of the N-tosyl residue produced (+)-loline, characterized as its dihydrochloride.

Toward a total synthesis of pristinamycin II(B); a chiron approach to a C-9/C-16 fragment

Copper(I)-catalysed addition of methyl Grignard reagent to the propagyl diol 8, which was efficiently prepared from S-malic acid proceeds with a perfect E stereoselectivity, the diol titus obtained being then converted into the title fragment by known met

Total syntheses of (+)-castanospermine and (+)-6-epicastanospermine

A divergent synthetic route to (+)-castanospermine 1 and (+)-6-epicastanospermine 2 has been developed via phenylselenoamidation of trichloroacetimidate derived from allylic alcohol 7, and dihydroxylations of trans-olefins 14 and 18 to dispose the three c