Angewandte Chemie - International Edition
Angewandte Chemie - International Edition
4 years ago

Enantioselective Total Synthesis of (−)-Deoxoapodine

Enantioselective Total Synthesis of (−)-Deoxoapodine
Tyler J. Mann, Amir H. Hoveyda, Taek Kang, Kolby L. White, Mohammad Movassaghi
The first enantioselective total synthesis of (−)-deoxoapodine is described. Our synthesis of this hexacyclic aspidosperma alkaloid includes an efficient molybdenum-catalyzed enantioselective ring-closing metathesis reaction for the desymmetrization of an advanced intermediate that introduces the C5-quaternary stereocenter. After C21-oxygenation, the pentacyclic core was accessed by electrophilic C19-amide activation and transannular spirocyclization. A biogenetically inspired dehydrative C6-etherification reaction proved highly effective to secure the F-ring and the fourth contiguous stereocenter of (−)-deoxoapodine with complete stereochemical control. A molybdenum-catalyzed enantioselective ring-closing metathesis reaction for the desymmetrization of an advanced intermediate is one of the key steps of the total synthesis of (−)-deoxoapodine. After C21-oxygenation, the pentacyclic core was accessed through amide activation and transannular spirocyclization. A dehydrative C6-etherification introduced the F-ring and the fourth contiguous stereocenter.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201708088

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