Acid‐Induced Rearrangement Reactions of Reduced Benzoquinone Cyclopentadiene Cycloadducts.

Abstract

Bridged compoundsBridged compounds Q 0060 Acid-Induced Rearrangement Reactions of Reduced Benzoquinone Cyclopentadiene Cycloadducts. -In the presence of strong acids diols of type (IV) undergo skeletal rearrangement to bicyclo[3.2.1]octane ring systems present in several natural products. Interestingly, treatment of the tetracyclic lactone (IX) with BF 3 etherate results in further rearrangement to the spiro lactone (X). -(EIPERT, M.; MAICHLE-MOESSMER, C.; MAIER*, M. E.; J. Org. Chem. 67 (2002) 24, 8692-8695; Inst. Org. Chem., Eberhard-Karls-Univ., D-72076 Tuebingen, Germany; Eng.) -Jannicke 18-066