Total Synthesis of Neoaltenuene

• Published in: European Journal of Organic Chemistry Vol. 2009; no. 14; pp. 2275 - 2282
• Main Authors: Altemöller, Martina, Podlech, Joachim
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag 01.05.2009; Wiley; Wiley-VCH
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; Chemistry, Organic; Cross‐coupling; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Palladium; Physical Sciences; Preparations and properties; Science & Technology; Total synthesis; Toxins; METABOLITES; ACID; FUNGUS; AZA-CLAISEN REARRANGEMENT; ATOM-TRANSFER CYCLIZATION; Palladium; Total synthesis; ALTENUENE; Cross-coupling; Toxins; ALTERNARIOL METHYL-ETHER; DERIVATIVES; CATALYSTS; MYCOTOXINS; Catalytic reaction; Alternaria; Palladium complex; Transition metal; Iodine Organic compounds; Fungi; Suzuki coupling; Benzoic acid derivatives; Organic iodine compounds; Toxin; Organic boronate; Cross reaction; Benzenic compound; Boron Organic compounds; Aromatic compound; Fungi Imperfecti; Chemical synthesis; Platinoid
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200900125

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.