Configuration-encoded 1,5-polyol synthesis allows precise control of remote stereogenic centers of polyketides such as bastimolide A, a nanomolar antiplasmodial compound. Asymmetric catalytic preparation of a key alpha-silyloxyaldehyde building block in a 3-step route from a hydrocarbon precursor is followed by iterative Julia-Kocienski couplings to generate the southern 1,5-polyol fragment of bastimolide A. Application of these versatile strategies and reactions to the northern fragment will be also be discussed, along with further progress toward bastimolide and analogs.

Control of remote stereogenic centers in bastimolide and analogs

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