1,9-Stereocontrol from 1,7-induction using an allylstannane followed by an Ireland-Claisen rearrangement

The 6-hydroxynona-2,7-dienylstananne 10 reacts with aldehydes after transmetallation with tin(IV) bromide with syn -selective 1,7-induction (1,7- syn : 1,7- anti = ca . 90 : 10). Ireland-Claisen rearrangements of the acetates 28a,b prepared from the syn -benzaldehyde product 14 , gave methyl (3 R ,11 R )-3-methyl-11-(arylmethoxy)-11-phenylundeca-4,8-dienoates 30a,b stereoselectively.