The chiral allylic stannane 1 adds to acrolein to yield the 1,5-syn diastereomer as a single stereoisomer. A subsequent sigmatropic rearrangement increased the distance between the stereocenters even further. This step was carried out en route to (±)-patulolide C.
Repeated use of the allylic stannane addition in an intramolecular sense was used in the synthesis of hemibrevetoxin B (one example is shown below). The pseudoequatorial positions of both "appendages" in the starting material lead to the observed stereoisomer.