Total synthesis of (+/-)-haouamine A.
The first total synthesis of the highly complex and potent anticancer agent haouamine A is reported through an eight-step sequence. Brevity of the sequence and complete control of chemo-, position-, and stereoselectivity (both planar and axial chirality) were possible through the invention of chemistry specifically tailored for the problems at hand, namely a cascade annulation proceeding via a hitherto unknown chemical entity for the indeno-tetrahydropyridine ring system as well as a pyrone-assisted stitching of the daunting bent-aromatic ring.
Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. pbaran@scripps.edu
Phil S
PS
Baran
Noah Z
NZ
Burns
D000478:Alkylation; D000818:Animals; D018360:Crystallography, X-Ray; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D014561:Urochordata / Q000737:chemistry; D000097566:Cyclophanes
D006576:Heterocyclic Compounds, 4 or More Rings; C474767:haouamine A; D000097566:Cyclophanes