4.8 Article

Stereocontrolled formal synthesis of (±)-platensimycin

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卷 10, 期 18, 页码 4049-4052

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AMER CHEMICAL SOC
DOI: 10.1021/ol801584r

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  1. Uehara Memorial Foundation
  2. Ministry of Education, Culture, Sports, Science, and Technology of Japan

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The caged structure of platensimycin, known as Nicolaou's key intermediate for total synthesis of platensimycin, was synthesized stereoselectively by using the following key steps: (i) diastereoselective Diels-Alder reaction between gamma-benzoyloxy enone and tert-butyldimethylsiloxydiene, (ii) formation of a dihydropyran ring by intramolecular catalytic oxypalladation, and (iii) transannular radical cyclization of monothloacetal with tributyltin hydride and AIBN.

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