The modular synthesis of 1,3-polyols using a chiral phosphine
oxide
building block is reported. This versatile building block works in
a repetitive way for the stereocontrolled synthesis of a tetraol key
intermediate, which serves for the first total synthesis of the potentially
anti-inflammatory natural product cryptoconcatone D. A new route toward
the chiral building block is also presented: Starting from 2-deoxy-d-ribose, the optimized sequence now makes the use of the building
block more attractive to practicing chemists again.
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