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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
Abstract 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.