Synthesis of C(3) benzofuran-derived bisaryl quaternary centers: approaches to diazonamide A.
[reaction: see text] Two complementary strategies for the synthesis of the diazonamide A bisaryl quaternary center are described. The first strategy relies upon an extremely facile tandem cyclopropanation/ring-opening sequence, which has proven amenable to chiral catalysis to provide enantioenriched material. The second strategy relies upon a more concise alkylation route ideal for material advancement.
Fuerst
D E
DE
Sterling Chemistry Laboratory, Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
Stoltz
B M
BM
Wood
J L
JL
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D007202:Indicators and Reagents; D010080:Oxazoles; C408862:diazonamide A