Development of Organoiron Methodology for Preparation of the Polyene Natural Product Macrolactin A
Methodology for the synthesis of the C7–C13 segment (19) and C14–C24 segment (41) of macrolactin A have been developed. Dicarbonyl(methyl 7-nitro-2E,4Z-heptadienoate)triphenylphosphineiron (19) is prepared by nucleophilic addition to a (1-methoxycarbonylpentadienyl)iron cation. The C23 stereocenter of 41 is established by introduction of a C20 stereocenter, chirality transfer from C20 to C23 followed by (diene)iron mediated selective ionic reduction of the C20 hydroxyl. The C15 stereocenter may be established by nitrile oxide–olefin cyclocondensation.
Bärmann, Heiko; Prahlad, Vadapalli; Tao, Chunlin; Yun, Young K.; Wang, Zhi; and Donaldson, William, "Development of Organoiron Methodology for Preparation of the Polyene Natural Product Macrolactin A" (2000). Chemistry Faculty Research and Publications. 77.