Asymmetric synthesis of the AB ring system of lactonamycin.
[reaction: see text] An enantiospecific synthesis of the AB fragment of lactonamycin (5) is achieved in eight steps from dimethyl D-tartrate. Ester enolate chemistry features prominently in the sequence.
Kelly
T Ross
TR
E. F. Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, USA. ross.kelly@bc.edu
Cai
Xiaolu
X
Tu
Bin
B
Elliott
Eric L
EL
Grossmann
Gilles
G
Laurent
Pierre
P
D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D007211:Indoles; D009285:Naphthoquinones; C102442:lactonamycin