STUDIES ON TOTAL SYNTHESIS OF STEROIDAL ANTIBIOTICS .3. GENERATION AND CORRELATION OF TETRACYCLIC DERIVATIVES FROM DEGRADATION OF FUSIDIC ACID AND TOTAL SYNTHESIS
STUDIES ON TOTAL SYNTHESIS OF STEROIDAL ANTIBIOTICS .3. GENERATION AND CORRELATION OF TETRACYCLIC DERIVATIVES FROM DEGRADATION OF FUSIDIC ACID AND TOTAL SYNTHESIS
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DOI：
10.1021/jo00428a002
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发表时间：
1977-01-01
影响因子：
3.6
通讯作者：
KAMATA, S
中科院分区：
文献类型：
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作者：
IRELAND, RE;GIGER, R;KAMATA, S
报道了呋喃西地酸降解为四环烯酮11的反应。这种转化的主要阶段是除去侧链，然后扩展5元D环。烯酮11的外消旋形式是由合成的烯二酮制备的。这种转化的中心特征是三氟化硼乙醚催化环氧化物重排，然后通过还原衍生的磷二酸酯除去C-6酮。外消旋和自然衍生的烯酮11的特性确定了所采用的合成计划的立体化学结果。
The degradation of fusidic acid to the tetracyclic enone 11 is described. The principle phases of this conversion are the removal of the side chain and then expansion of the 5-membered D ring. The racemic form of the enone 11 was prepared from the synthetic enedione. The central feature of this transformation entails the boron trifluoride etherate catalyzed rearrangement of the epoxide and then removal of the C-6 ketone through reduction of the derived phosphorodiamidate. The identity of the racemic and naturally derived enones 11 establishes the stereochemical outcome of the synthetic plan employed.