Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 51, Pages 23089-23093Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202010759
Keywords
alkaloids; C-H functionalization; haloetherification; oxidation; total synthesis
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Funding
- Drug Discovery and Life Science Research (BINDS) from AMED [JP19am0101100]
- JSPS KAKENHI [JP18H04379, JP18H04231, JP18H04642, 18H02549, 17K08204]
- Grants-in-Aid for Scientific Research [17K08204, 18H02549] Funding Source: KAKEN
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We have established a highly convergent 10-step route for the total synthesis of (-)-deoxoapodine, which is a hexacyclic aspidosperma alkaloid. The quaternary C5 center of the characteristic tetrahydrofuran ring was constructed by a chiral-phosphoric-acid-catalyzed enantioselective bromocycloetherification in a 5-endofashion and subsequent allylation by using the Keck protocol. Construction of the aspidosperma skeleton features the formation of a nine-membered lactam by a catalytic C-H palladation/alkylation cascade at the indole 2-position and an iron-catalyzed oxidative transannular reaction at a late-stage of the synthesis.
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