Synthesis and Stereochemical Revision of Violaceoid E, a Polyoxygenated Cyclohexanoid Natural Product Isolated from Aspergillus violaceofuscus Gasperini.

The first concise synthesis of the proposed structure of violaceoid E, possessing a cis-diol moiety, has been achieved. However, the spectroscopic data of the synthetic compound were inconsistent with those of the natural product, suggesting that the genuine violaceoid E might be a trans-diol. An efficient synthesis of our proposed trans-diol-type violaceoid E has also been achieved, enabling the establishment of the absolute configuration of natural violaceoid E.