The asymmetric Maitland-Japp reaction and its application to the construction of the C1-C19 bis-pyran unit of phorboxazole B.
The synthesis of the C1-C19 bis-pyran unit of phorboxazole B has been achieved. The key pyran rings were constructed by means of an asymmetric Maitland-Japp reaction and a second Maitland-Japp resolution/cyclization reaction. The longest linear sequence was 14 steps, and the C1-C19 bis-pyran unit was formed in an impressive 10.4% yield.
Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK. paul.clarke@york.ac.uk
Paul A
PA
Clarke
Soraia
S
Santos
Nimesh
N
Mistry
Laurence
L
Burroughs
Alexander C
AC
Humphries
D003500:Cyclization; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry
D006576:Heterocyclic Compounds, 4 or More Rings; D010080:Oxazoles; D011714:Pyrans; C408887:phorboxazole A