A Model Study towards a Conceptually New Synthetic Entry into the Seco‐ and Heteroyohimbine Alkaloid Families | Zendy

Vogelsang Thomas | Zendy; Borschberg HansJürg | Zendy

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A Model Study towards a Conceptually New Synthetic Entry into the Seco‐ and Heteroyohimbine Alkaloid Families

Author(s) -

Vogelsang Thomas,

Borschberg HansJürg

Publication year - 2003

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200390303

Subject(s) - chemistry , moiety , alkaloid , derivative (finance) , diene , yield (engineering) , stereochemistry , combinatorial chemistry , organic chemistry , natural rubber , materials science , financial economics , economics , metallurgy

A model study is presented that paves the way to a new and flexible synthetic approach towards the seco‐ and heteroyohimbine alkaloid class. The key step involves a highly diastereoselective Cope rearrangement of an ( E , E )‐azacyclodeca‐3,7‐diene grafted onto a 3‐ethylindole moiety to furnish a trans ‐3,4‐divinylpiperidine derivative in 83% yield.

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