171231-65-5Relevant articles and documents
Application of radical cyclisation/iodine atom transfer to the chiral synthesis of (-)-methylenolactocin
Mawson, Simon D.,Weavers, Rex T.
, p. 11257 - 11270 (2007/10/02)
Methylenolactocin, an antitumour antibiotic, has been synthesized through an efficient radical cyclisation process on a chiral iodo acetylene ester. Chiral iodohydrins may be formed by regioselective opening of a chiral epoxy ester, prepared by Sharpless epoxidation. C-2 opening is achieved with TMSCl/NaI and C-3 attack with MgI2. Subsequent esterification of the 2-iodo compound by reaction with substituted propynoyl triflates gives the key iodo acetylenic esters. This route is highly adaptable to the synthesis of analogues.
