Total Synthesis Of Coriandrone B & Studies On The Total Synthesis Of Rubromycin

This thesis aims at the studies on First total synthesis of natural product Coriandrone B and studies on the synthesis ofγ-Rubromycins, which consists of the following two chapters: Chapter 1. First total synthesis of natural product Coriandrone BThe character of configuration and synthesis strategy of Coriandrone B was introduced briefly. Synthesis of racemic Coriandrone B and (+) Coriandrone B were studid. The pyran was formed in a reaction of Phenolic hydroxyl and epoxide under the acid conditions. ortho Lithiation of amide and alkylation of (S)-(-)-propylene oxide which followed the lactone cyclization led to isocoumarin ring. Finaly, Coriandrone B and (+) Coriandrone B have been achieved from readily available 2,4-dihydroxybenzoic acid with 14 steps and 16 steps respectively.Chapter 2. Studies on the synthesis of natural productγ-RubromycinsThe isolation, structural characterization, biological activities, and total syntheses of Rubromycins were introduced comprehensively. Two routes toward synthesis of natural productγ-Rubromycins were designed and tried. The first scheme is based on a reaction which involves Gold-Catalyzed Double Intramolecular Alkyne Hydroalkoxylation to achieve the Synthesis of the Bis-benzannelated Spiroketal Core of Rubromycins. We designed a simulation reaction, and several key intermediates was obtained, such as 84; key intermediates 93 by coupling reaction. In the second scheme, we hope to aplly Palladium-Cactalyzed Intramolecular Wacker Reaction to complete the Synthesis of the Bis-benzannelated Spiroketal Core of Rubromycins. We also designed a simulation reaction, and several key intermediates were obtained, such as 88,89,98 and 93. Related work is still in progress.