Stereoselective total synthesis of dihydrocorynantheol |
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Authors: | Deiters Alexander Martin Stephen F |
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Affiliation: | Department of Chemistry and Biochemistry, The University of Texas, Austin 78712, USA. |
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Abstract: | [reaction: see text] A stereoselective synthesis of the indole alkaloid dihydrocorynantheol (1) from indole-3-acetic acid has been achieved by a sequence involving 9 as a key intermediate. The synthesis of the unsaturated lactam ring in 9 highlights a series of catalytic organometallic reactions featuring two ring-closing metatheses and a zirconocene-catalyzed carbomagnesation. Since no protecting groups were used, the present synthesis of 1 is exceedingly concise, consisting of only eight distinct operations. |
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