Short asymmetric synthesis of (-)- and (+)-cis-lauthisan.
The asymmetric synthesis of both enantiomers of cis-lauthisan (3) is achieved in only six steps from diethyl pimelate (4), the key steps being the diastereodivergent reduction of beta-ketosulfoxide 7 and the highly cis-stereoselective Et(3)SiH/TMSOTf-promoted reductive cyclization of enantiopure hydroxy sulfinyl ketones (S)-14 and (R)-14.
Carreño
M Carmen
MC
Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, Spain. carmen.carreno@uam.es
Des Mazery
Renaud
R
Urbano
Antonio
A
Colobert
Françoise
F
Solladié
Guy
G
D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D044722:Laurencia / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D004988:Ethers, Cyclic; C471499:lauthisan