Premium
First asymmetric synthesis of (–)‐lintetralin via intramolecular Friedel‐Crafts‐type cyclization
Author(s) -
Enders Dieter,
del Signore Giuseppe,
Berner Otto Mathias
Publication year - 2003
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10242
Subject(s) - chemistry , friedel–crafts reaction , intramolecular force , type (biology) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , ecology , biology
The asymmetric synthesis of an aryltetralin lignan, (–)‐lintetralin, was achieved with an overall yield of 29% with seven steps. Key features of the synthesis are an asymmetric Strecker reaction, a diastereoselective Michael addition of the lithiated amino nitrile product to 5 H ‐furan‐2‐one, and an intramolecular carbocationic cyclization to provide the desired ring skeleton with the correct configuration. Chirality 15:510–513, 2003. © 2003 Wiley‐Liss, Inc.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom