Synthesis of 2‐Azabicyclo[ m.n .0]–Alkanes and Their Application towards the Synthesis of  Strychnos  and  Stemona  Classes of Alkaloids | Zendy

Majumder Binoy | Zendy; Pandey Ganesh | Zendy

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Synthesis of 2‐Azabicyclo[ m.n .0]–Alkanes and Their Application towards the Synthesis of Strychnos and Stemona Classes of Alkaloids

Author(s) -

Majumder Binoy,

Pandey Ganesh

Publication year - 2020

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.202000507

Subject(s) - chemistry , strychnos , bicyclic molecule , ring (chemistry) , stereochemistry , azepine , medicinal chemistry , organic chemistry , alkaloid

2‐Azabicyclo[ m.n .0]alkane ring systems, the conceptual precursors towards the synthesis of Strychnos and Stemona classes of alkaloids, were synthesized from tert ‐butyl 2‐(phenylsulfonyl)‐7‐aza‐bicyclo[2.2.1]hept‐2‐ene‐7‐carboxylate by alkyl Grignard reaction and intramolecular cyclisation of the in situ generated ring opening product 2 . The synthesized cis ‐hexahydroindole 3 and cis ‐octahydro‐benzo[ b ]azepine 5 scaffolds were utilized to construct the advanced intermediates 25 and 35 , respectively, towards the synthesis of the corresponding Strychnos and Stemona classes of alkaloids.

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