Enantioselective Total Synthesis of (-)-Deoxoapodine

Title
Enantioselective Total Synthesis of (-)-Deoxoapodine
Authors
강택Kolby L. WhiteTyler J. MannAmir H. HoveydaMohammad Movassaghi
Issue Date
2017-10
Publisher
Angewandte Chemie international edition
Citation
VOL 56, NO 44-13860
Abstract
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.
URI
http://pubs.kist.re.kr/handle/201004/67150
ISSN
1433-7851
Appears in Collections:
KIST Publication > Article
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