Tetrahedron p. 11257 - 11270 (1995)
Update date:2022-08-02
Topics:
Mawson, Simon D.
Weavers, Rex T.
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.
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