89578-12-1Relevant articles and documents
Synthetic method of methylthiomethyl
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Paragraph 0101; 0102, (2019/02/06)
The invention provides a synthetic method of methylthiomethyl. The synthetic method comprises the step of carrying out crossed dehydrogenation on a carboxylic acid compound and dimethylsulfoxide in the presence of nitrogen and organic amine, so as to gene
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.