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Synthesis of iso-C15 4, iso-C16 5, and iso-C17 6 fatty acids from pentadecanolide (15). Reagents and conditions: (a) MeMgBr, THF, 98%; (b) BF3·Et2O, Et3SiH, CH2Cl2, 96%; (c) KMnO4, Bu4NBr, AcOH, H2O, 95% for 6, 93% for 5; 86% for 4; (d) NaH, CS2 then MeI; (e) reflux, 89% for 19 over 2 steps from 17, 98% for 22 over 2 steps from 20; (f) BH3·SMe2, THF, 78%.
