Total Synthesis of (+)‐Colletodiol from (S,S)‐Tartrate and (R)‐3‐Hydroxybutanoate

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Abstract
The macrodiolide antibiotic (+)‐colletodiol (7, Scheme 1) was synthesised. The configuration was thus proven to be (6R,11R,12R,14R). – Key intermediates (Schemes 9 and 10) are the two hydoxy acids 43 and 64, which were prepared from dimethyl (S,S)‐tartrate in 20% overall yield (12 steps) and from (R)‐3‐hydroxybutanoate in 57% overall yield (6 steps), respectively. The two hydroxy acids were cyclised to give, after deprotection, the title compound. – Our investigations led to the production of a large number of chiral building blocks, many of them in different stereoisomeric forms.

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