NEW SYNTHETIC REAGENTS, ALLENYLMETHYLSILANES AND THEIR UTILIZATION FOR NATURAL PRODUCT SYNTHESIS

Allenylmethylsilanes have not received so much attention from a synthe tic point of view although we can expect various allylsilane and allen e chemistry with these molecules. We were, therefore, interested in pr obing whether we can utilize allenylmethylsilanes as a versatile synth etic reagent. This article deals with (1) preparation of allenylmethyl silanes, (2) their Lewis acid catalyzed reactions with aldehydes or ac etals leading to either racemic or chiral alkyl(1,3-butadien-2-yl)meth anols, (3) mono-epoxidation of alkyl(1, 3-butadien-2-yl) methanols, ge nerating a new type of epoxy alcohol chiral building blocks, (4) react ions of allenylmethylsilanes with iodine leading to 3-iodo-3-iodomethy lallyl-silanes and preparation of 2-iodo-1,3-butadienes, and (5) synth esis of natural products based on the above-mentioned reactions.