Organocatalytic Asymmetric Mannich Cyclization of Hydroxylactams with Acetals: Total Syntheses of (−)‐Epilupinine, (−)‐Tashiromine, and (−)‐Trachelanthamidine | Zendy

Koley Dipankar | Zendy; Krishna Yarkali | Zendy; Srinivas Kyatham | Zendy; Khan Afsar Ali | Zendy; Kant Ruchir | Zendy

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Organocatalytic Asymmetric Mannich Cyclization of Hydroxylactams with Acetals: Total Syntheses of (−)‐Epilupinine, (−)‐Tashiromine, and (−)‐Trachelanthamidine

Author(s) -

Koley Dipankar,

Krishna Yarkali,

Srinivas Kyatham,

Khan Afsar Ali,

Kant Ruchir

Publication year - 2014

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201407185

Subject(s) - yield (engineering) , chemistry , acetal , mannich reaction , bicyclic molecule , enantioselective synthesis , organic chemistry , derivative (finance) , stereochemistry , catalysis , materials science , metallurgy , economics , financial economics

An asymmetric, organocatalytic, one‐pot Mannich cyclization between a hydroxylactam and acetal is described to provide fused, bicyclic alkaloids bearing a bridgehead N atom. Both aliphatic and aromatic substrates were used in this transformation to furnish chiral pyrrolizidinone, indolizidinone, and quinolizidinone derivatives in up to 89 % yield and 97 % ee . The total syntheses of (−)‐epilupinine, (−)‐tashiromine, and (−)‐trachelanthamidine also achieved to demonstrate the generality of the process.

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