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Upstream product

• 3669-80-5 11-hydroxyundecanoic acid 
• 2834-05-1 11-bromoundecanoic acid 
• 63632-65-5 11-iodo-undecanoic acid 
• 109182-97-0 Acrylic acid 8-iodo-octyl ester 
• 24724-07-0 methyl 11-hydroxyundecanoate 

Relevant academic research and scientific papers

An improved and novel approach to macrolactonisation using di-tert-butyl dicarbonate

A new, facile, mild and simple method for the synthesis of macrolides was achieved from ω- hydroxy acids using di-tertbutyl dicarbonate (Boc2O), a cheap and commercially available reagent. A wide range of substrates were tested and give good yield of lactones. The effect of various simple bases on the yield of the macrolactonisation reaction was also studied.

Macrocyclisation of macrodiolide with dimethylaluminium methaneselenolate

Dimethylaluminium methaneselenolate (Me2AlSeMe, 1) acts as an acyl transfer agent for esterification. In cases of direct macrolactonisation (n = 10-12), this selenium-aluminium complex preferentially creates symmetric macrodiolides rather than macrolides. The factors determining macrodilactonisation were investigated and applied toward the total synthesis of norpyrenophorin, which result in a macrodilactonisation yield of 64 %. Dimethylaluminium methaneselenolate (Me2AlSeMe, 1) acts as an acyl transferagent for esterification. In cases of direct macrolactonisation (n = 10-12), this selenium-aluminium complex preferentiallycreates symmetric macrodiolides rather than macrolides. The factors determining macrodilactonisation were investigated and applied toward the total synthesis of nor-pyrenophorine. Copyright

A new method for the lactonization of ω-hydroxy carboxylic acids with Di-2-thienyl carbonate by the promotion of DMAP and iodine

Successive reactions of ω-hydroxycarboxylic acids with an equimolar amount of di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino)pyridine (DMAP) followed by an addition of 2-4 equimolar amounts of iodine afforded the corresponding lactones in good to high yields. Copyright

Efficient method for the lactonization of ω-hydroxycarboxylic acids with di-2-thienyl carbonate by the promotion of catalytic amounts of DMAP and Hf(OTf)4

An efficient method for the synthesis of macrolides from ω-hydroxycarboxylic acids is established by using an equimolar amount of di-2-thienyl carbonate (2-DTC) and catalytic amounts of 4-(dimethylamino) pyridine (DMAP) and group 4 metal triflates such as hafnium(IV) trifluoromethanesulfonate (Hf(OTf)4). Copyright

A new method for the synthesis of carboxylic esters and lactones with di-2-thienyl carbonate (2-DTC) by the promotion of DMAP and iodine

The esterification of carboxylic acids with alcohols by using di-2-thienyl carbonate (2-DTC) in the presence of a catalytic amount of 4-(dimethylamino) pyridine (DMAP) proceeded smoothly to afford the corresponding esters in good-to-high yields along with 2(5H)-thiophenone. This esterification was accelerated by the addition of an equimolar amount of iodine to afford the esters in higher yields within a shorter reaction time. Further, cyclization of ω-hydroxycarboxylic acids with an equimolar amount of 2-DTC in the presence of a catalytic amount of DMAP, followed by the addition of 1-4 equimolar amounts of iodine, afforded the corresponding lactones in good-to-high yields under mild conditions. This method was successfully employed in the synthesis of erythro-aleuritic acid lactone.

A new method for the polymer-supported synthesis of cyclic oligoesters for potential applications in macrocyclic lactone synthesis and combinatorial chemistry

Attachment of ω-hydroxyalkanecarboxylic acids to Merrifield beads followed by treatment with a catalytic amount of di-n-butyltin oxide in chlorobenzene at 133 °C for 4-18 h brought about the formation of the corresponding cyclic oligomers (COs) as the mai

New and efficient method for the preparation of medium-sized lactones from the corresponding ω-hydroxycarboxylic acids

Medium-sized lactones are prepared in good yields on treating monomeric cyclic silyl siloxycarboxylates, prepared in situ from ω-hydroxycarboxylic acids and 1,2-bisdimethylsilylbenzene using RhCl(PPh3)3 catalyst, with an active catalyst of dimethylsilylbis(trifluoromethanesulfonate).

Scandium trifluoromethanesulfonate as an extremely active Lewis acid catalyst in acylation of alcohols with acid anhydrides and mixed anhydrides

Scandium trifluoromethanesulfonate (triflate), which is commercially available, is a practical and useful Lewis acid catalyst for acylation of alcohols with acid anhydrides or the esterification of alcohols by carboxylic acids in the presence of p-nitrobenzoic anhydrides. The remarkably high catalytic activity of scandium triflate can be used for assisting the acylation by acid anhydrides of not only primary alcohols but also sterically-hindered secondary or tertiary alcohols. The method presented is especially effective for selective macrolactonization of ω-hydroxy carboxylic acids.

A Novel Method for the Preparation of Macrolides from ω-Hydroxycarboxylic Acids

An efficient method for the synthesis of macrolides directly from ω-hydroxycarboxylic acids is established by using 4-(trifluoromethyl)benzoic anhydride and a catalytic amount of active titanium(IV) salts together with chlorotrimethylsilane under mild conditions.

A New Synthetic Method of Macrocyclic Lactones from ω-Iodoalkylacrylates

When the photostimulated cyclization reaction of ω-iodoalkylacrylates was performed in the presence of metal hydride complexes such as sodium cyanoborohydride (NaBH3CN), sodium borohydride (NaBH4) and potassium borohydride (KBH4), the corresponding macrocyclic lactones were produced.The use of NaBH3CN led to the highest yield of lactones.