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      Novel stereocontrolled approach to syn- and anti-oxepene-cyclogeranyl trans-fused polycyclic systems: asymmetric total synthesis of (-)-Aplysistatin, (+)-Palisadin A, (+)-Palisadin B, (+)-12-hydroxy-palisadin B, and the AB ring system of adociasulfate-2 and toxicol A.

      1 ,
      Chemistry (Weinheim an der Bergstrasse, Germany)
      Wiley

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          Abstract

          A new stereocontrolled method for the formation of trans-anti cyclogeranyl-oxepene systems is described. The demanding stereochemistry is secured by stereoselective coupling of a cyclogeranyl tertiary alcohol with a 1,2-unsymmetrically substituted epoxide, while the formation of the highly strained oxepene is achieved employing ring-closing metathesis. Since the stereochemistry of the trans-fused 6,7-ring system is determined by the epoxide, the method also allows the construction of trans-syn 6,7-ring systems. This approach leads to the synthesis of the AB fragment of Adociasulfate-2 and Toxicol A, for the first time. The flexibility and efficiency of the presented strategy is demonstrated by the total asymmetric synthesis of (-)-Aplysistatin, (+)-Palisadin A, (+)-12-hydroxy-Palisadin B, and (+)-Palisadin B, employing two similar key intermediates.

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          Author and article information

          Journal
          Chemistry
          Chemistry (Weinheim an der Bergstrasse, Germany)
          Wiley
          0947-6539
          0947-6539
          Aug 06 2004
          : 10
          : 15
          Affiliations
          [1 ] Chemistry Laboratories, Agricultural University of Athens, Iera Odos 75, Athens 118 55, Greece. ecoula@chem.demokritos.gr
          Article
          10.1002/chem.200400407
          15281167
          7d0339a9-57f9-41f3-9d62-2c0b1fe2144f
          History

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