Total Synthesis of Neoaltenuene

The total synthesis of neoaltenuene, a toxin produced by alternaria fungi, has been achieved for the first time in 14 steps in a yield of 10 % starting from quinic acid and phloroglucinic acid, the longest linear sequence consisting of 10 steps. The key reaction was a palladium‐catalyzed Suzuki‐type coupling of an arene boronate with an iodinated cyclohexene.4a‐epi‐Neoaltenuene, a non‐natural isomer has been synthesized similarly. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) The total synthesis of Alternaria metabolite neoaltenuene has been achieved for the first time in 14 steps in a yield of 10 % starting from quinic acid and phloroglucinic acid. The key reactions are a palladium‐catalyzed Suzuki‐type coupling and apalladium(II)‐catalyzed [3,3]‐sigmatropic rearrangement.