Synthesis of (±)-oleocanthal via a tandem intramolecular Michael cyclization–HWE olefination

BJ English, RM Williams

Index: English, Brandon J.; Williams, Robert M. Tetrahedron Letters, 2009 , vol. 50, # 23 p. 2713 - 2715

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Citation Number: 11

Abstract

The secoiridoids are a class of plant-derived monoterpenes containing the substituted pyran core of secologanin (1). This class of natural products arises in biological systems from the oxidative cleavage of the loganin skeleton (2) by the cytochrome P450 enzyme secologanin synthase (Fig. 1). 1 Secologanin then undergoes various modifications to produce a wide array of structures displaying diverse biological activities including analgesic 2 , anti-inflammatory 3 , anti- ...