Approach to the hyacinthacines: first non-chiral pool synthesis of (+)-hyacinthacine A1.
The first non-chiral pool total synthesis of (+)-hyacinthacine A(1) is described. This synthesis is based on an effective [2 + 2] cycloaddition of dichloroketene to a Stericol-based enol ether, a diastereoselective dihydroxylation, and an efficient Tamao-Fleming oxidation.
Reddy
P Venkatram
PV
Département de Chimie Moléculaire (SERCO) UMR-5250, ICMG FR-2607, CNRS Université Joseph Fourier, BP-53, 38041, Grenoble Cedex 9, France.
Veyron
Amaël
A
Koos
Peter
P
Bayle
Alexandre
A
Greene
Andrew E
AE
Delair
Philippe
P
D003500:Cyclization; D004000:Dichloroethylenes / Q000737:chemistry; D015394:Molecular Structure; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004000:Dichloroethylenes; D011763:Pyrrolizidine Alkaloids; C508850:hyacinthacine A1; C039586:dichloroketene