A NOVEL STRATEGY FOR THE STEREOSELECTIVE TOTAL SYNTHESIS OF C-17 SPIRO STEROIDS - TOTAL SYNTHESIS OF 19-NORCANRENONE, A FORMAL TOTAL SYNTHESIS OF 19-NORSPIRONOLACTONE
A NOVEL STRATEGY FOR THE STEREOSELECTIVE TOTAL SYNTHESIS OF C-17 SPIRO STEROIDS - TOTAL SYNTHESIS OF 19-NORCANRENONE, A FORMAL TOTAL SYNTHESIS OF 19-NORSPIRONOLACTONE
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DOI：
10.1021/ja00217a040
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发表时间：
1988-04-27
影响因子：
15
通讯作者：
KAMETANI, T
中科院分区：
文献类型：
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作者：
NEMOTO, H;FUJITA, S;KAMETANI, T
烯烃苯并环丁烯原位热裂解生成烯烃-邻喹啉二甲烷分子内（4 +2）环加成反应，立体选择性地生成a -或b -芳烃- C-17甾体。这是一个新的和一般的方法立体选择性合成具有重要生物学意义的C-17螺旋甾体。该方法得到了19-去甲醌的全合成，构成了19-去甲螺内酯的正式全合成。
The intramolecular (4 +2) cycloaddition reactions of olefinic o-quinodimethanes, generated in situ by the thermolysis of olefinic benzocyclobutenes, lead stereoselectively to A-nor B-aromatic C-17 spiro steroids. This is a new and general methodology for the stereoselective synthesis of biologically important C-17 spiro steroids. This method yields the total synthesis of 19-norcanrenone, constituting a formal total synthesis of 19-norspironolactone.