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Formal Total Synthesis of (+)-Wortmannin Using Catalytic Asymmetric Intramolecular Aldol Condensation Reaction by Hiroki Shigehisa; Takashi Mizutani; Shin-ya Tosaki; Takashi Ohshima; Masakatsu Shibasaki is a Chemistry article available to read on EtoBox.
What is Formal Total Synthesis of (+)-Wortmannin Using Catalytic Asymmetric Intramolecular Aldol Condensation Reaction about?
A catalytic process for the synthesis of optically active C4-substituted tetrahydroindandiones using an asymmetric intramolecular aldol condensation reaction was developed. When 30 mol% of phenylalanine and 50 mol% of pyridinium p-toluenesulfonate were used under highly concentrated conditions, a variety of C4-substituted tetrahydroindandiones and octahydronaphthalenediones were obtained in high yield (up to 89% yield) and high enantiomeric excess (up to 94% ee). One of the products was successfully transformed into the key intermediate for the synthesis of the phosphatidylinositol 3-kinase inhibitor wortmannin, achieving formal total synthesis of (C)-wortmannin.
Who reads Formal Total Synthesis of (+)-Wortmannin Using Catalytic Asymmetric Intramolecular Aldol Condensation Reaction?
It is typically read by researchers, students, and practitioners in Chemistry.
- Author
- Hiroki Shigehisa; Takashi Mizutani; Shin-ya Tosaki; Takashi Ohshima; Masakatsu Shibasaki
- Publisher
- Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4020)
- Published
- 2005
- Language
- EN
- Field
- Chemistry (Physical Sciences)