70950-06-0Relevant articles and documents
Synthesis of Elongated Esters from Alkenes
Miura, Tomoya,Funakoshi, Yuuta,Nakahashi, Junki,Moriyama, Daisuke,Murakami, Masahiro
, p. 15455 - 15459 (2018/10/31)
A convenient method for synthesizing elongated aliphatic esters from alkenes is reported. An (alkoxycarbonyl)methyl radical species is generated upon visible-light irradiation of an ester-stabilized phosphorus ylide in the presence of a photoredox catalyst. This radical species adds onto the carbon–carbon double bond of an alkene to produce an elongated aliphatic ester.
Radical-mediated Carbonylation of Alkyl Iodides in Aqueous Media
Sugiura, Masaharu,Hagio, Hiroyuki,Kobayashi, Shu
, p. 898 - 899 (2007/10/03)
Radical-mediated single carbonylation of alkyl iodides furnishing carboxylic acids proceeded in water using phosphinic acid as a radical initiator in the presence of a surfactant (CTAB). On the other hand, formation of double carbonylation product (α-keto carboxylic acid) along with single carbonylation product was observed for the first time, when the reaction was carried out in aqueous ethanol without any surfactants.
Total Synthesis of a Macrocyclic Pyrrolizidine Alkaloid, (+/-)-Integerrimine, Utilizing an Activable Protecting Group
Narasaka, Koichi,Sakakura, Toshiyasu,Uchimaru, Tadafumi,Guedin-Vuong, Denis
, p. 2954 - 2961 (2007/10/02)
A new esterification reaction has been developed utilizing a (methylthio)methyl (MTM) group as an activable protecting group of carbocyclic acid.A total synthesis of a 12-membered pyrrolizidine alkaloid, (+/-)-integerrimine (1), has been achieved by applying the above method to formation of the macrocyclic bislactone skeleton.The acid anhydride (16b) of the integerrinecic acid derivative was coupled with lithium alkoxide of retronecine silyl ether (5b) in the presence of DMAP to afford the α,β-unsaturated ester.Oxidation of the MTM group afforded an active (methylsulfonyl)methyl ester (28b), which cyclized to give the macrocyclic bislactone 29.