Stannyl–cupration of acetylenes followed by electrophilic attack with a variety of electrophiles gives vinylstannanes.

Oxygen heterocycles are units that are abundant in a great number of marine natural products. Among them, marine polyketides containing tetrahydrofuran rings have attracted great attention within the scientific community due to their challenging structures and promising biological activities. An overview of the most important marine tetrahydrofuran polyketides, with a focused discussion on their isolation, structure determination, approaches to their total synthesis, and biological studies is provided.

The tert-butyldiphenylsilyl-cuprate 2 reacts with acetylenes 1 and 5–10 to give vinyl-cuprates 3 and 11, which react with electrophiles to give the vinylsilanes 4 and 12–17 carrying the relatively hindered and hence unreactive tert-butyldiphenylsilyl group. In comparative tests, the tert-butyldiphenylsilyl group shows some properties that are usefully different from those of relatively unhindered silyl groups and others that are similar.