A stereoselective total synthesis of antibiotic ([plus-minus])-LL-Z 1271 [proportional to]

The stereoselective total synthesis of (plus-minus)-LL-Z 1271[proportional to] (1) is presented. The general synthetic scheme is shown below. The synthetic approach presented incorporates a new stereo-selective reductive alkylation reaction, a new method of lactonization, and a novel methanolysis reaction to give the title compound (1) and its anomer (2) in a favorable ratio.