Synthetic Studies toward Aplysiasecosterol A: Concise Synthesis of the Tricyclic Core and Its Reactions for Introduction of the D Ring Fragment

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  • Ohyoshi Takayuki
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Tano Hikaru
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Kigoshi Hideo
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba

Abstract

<p>Aplysiasecosterol A, a 9,11-secosteroid, has a unique tricyclic γ-diketone skeleton including a hemiacetal. The concise and efficient synthesis of the tricyclic core was developed by using pseudo-desymmetrizing acetalization and acyl radical cyclization. Toward the total synthesis, an efficient method for the introduction of the D ring fragment was developed by using an organocuprate.</p>

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