Completion of synthesis of Hirsutene and Capnellene
12 Outubro 2016, 14:00 • Christopher David Maycock
Formation of alcohols by reduction of carboxylic acids. Activation of primary and secondary hydroxyl groups to nucleophilic attack using sulphonate esters. Formation of halides (iodides) by nucleophilic substitution. Use of alkynes and acetylene derivatives for the formation of C-C bonds. Ease of formation of carbanions from terminal alkynes (acidity). Reactivity of neopentyl groups. Generation of free radicals and their chain reactions.
Use of AIBN/heat as initiator and tin reagents as propagators. Tandem radical reactions and the formation of Hirsutene. Reduction of organic halides using tin reagents.
Capnellene a similar structure. SN2' strategy for the formation of quaternary centre with correct relative stereochemistry. Bayer-Villager rearrangement for the transformation of cyclic ketones into lactones. Acid catalysed (carbocationic) rearrangement of strained systems to form bicyclic lactones. Stereoselective SN2' reactions revisited. Iodolactonisation.