1224714-08-2Relevant academic research and scientific papers
Conversion of Ester Moieties to 4-Bromophenyl Groups via Electrocyclic Reaction of Dibromocyclopropanes
Ueda, Kyosuke,Umihara, Hirotatsu,Yokoshima, Satoshi,Fukuyama, Tohru
, p. 3191 - 3193 (2015)
(Chemical Equation Presented) Conversion of ester moieties into 4-bromophenyl groups was effected by means of a four-step protocol: a Grignard reaction of the ester with allylmagnesium halides, a ring-closing metathesis, dibromocyclopropanation, and an electrocyclic reaction of the dibromocyclopropanes.
Synthesis of the alkaloid tyroscherin by an aldol/Curtius strategy
Ugele, Markus,Maier, Martin E.
supporting information; experimental part, p. 2633 - 2641 (2010/05/01)
The alkaloid tyroscherin (2), which contains a vicinal anti-amino alcohol subunit was prepared from 4-hydroxyphenylpropionic acid (5) and meso-diol 9. After desymmetrization of diol 9 and suitable protecting group manipulations, one terminus was extended via a Claisen rearrangement giving rise to enoate ent-15. The missing carbon on the other end could be incorporated using MeMgCl/CuBr·SMe2 leading eventually to aldehyde ent-22. The acylated oxazolidinone 32 derived from acid 5 and aldehyde ent-22 were combined in an aldol reaction. A subsequent Curtius rearrangement on the carboxylic group furnished the amino function of tyroscherin (2). In a proof of concept study the same strategy was used to prepare tyroscherin analog 28.
