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Approaches to the synthesis of cytochalasans. Part 10 . Cuprates as reagents for the formation of CC bonds
Author(s) -
Matthes Michael,
Tamm Christoph
Publication year - 1991
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.19910740720
Subject(s) - chemistry , reagent , cuprate , yield (engineering) , bicyclic molecule , derivative (finance) , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , superconductivity , thermodynamics , physics , quantum mechanics , economics , financial economics
Based upon our novel concept for the total synthesis of cytochalasans, the model lactams 2–9 were treated with Bu 2 Cu(CN)Li 2 . The results of these conversions vary much from those obtained with Ph 2 Cu(CN)Li 2 , demonstrating the uncertainty of predictions in cuprate chemistry. The bicyclic compound 20 was prepared in good yield. However, all attempts to convert p ‐toluenesulfonate 20 into the Ph‐substituted derivative 21 , an intermediate for the synthesis of cyiochulusm B(1) , have failed so far.