Scalable, catalytic asymmetric synthesis of syn, anti stereotriad building blocks for polypropionate antibiotics.

[reaction: see text] Asymmetric catalysis and chirality transfer by the 2,3-Wittig rearrangement were combined to provide a syn, anti stereotriad-containing olefinic alcohol in five steps from inexpensive starting materials. Development of this compound, a versatile intermediate for polypropionate synthesis, gave known building blocks for discodermolide.