Journal
ORGANIC LETTERS
Volume 10, Issue 18, Pages 4049-4052Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801584r
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Funding
- Uehara Memorial Foundation
- 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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