Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 37, Pages 13120-13126Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201501859
Keywords
alkaloids; asymmetric synthesis; rearrangement; spiro compounds; total synthesis
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Funding
- DST, New Delhi
- CSIR, New Delhi
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A novel bridgehead-substituted aza-bicyclic framework has been designed and developed in both enantiomeric forms through an asymmetric desymmetrization reaction. Strategic exploitation of the ring strain in the aza-bicyclic framework has been utilized for the construction of the chiral aza-quaterenary scaffolds by selective bond fragmentation processes. Furthermore, a strategically designed precursor is employed for selective bond cleavage to initiate a cascade rearrangement for the total synthesis of the 1-azaspirotricyclic marine alkaloids (+)-cylindricinesC, D, and E, as well as (-)-lepadiformineA. An oxidation/retro-aldol/aza-Michael sequence generated three new chiral centers with the required configuration in one pot.
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