The first total synthesis of (+/-)-scopadulin, an antiviral aphidicolane diterpene.
[reaction: see text] The first total synthesis of (+/-)-scopadulin was accomplished by a stereoselective construction of a quaternary carbon at C-4, conversion of the hindered cyano group to a methyl group via our novel reaction for conversion of primary aliphatic amines into alcohols, and a highly chemo- and stereoselective methylation at C-16.
Rahman
S M
SM
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Ohno
H
H
Murata
T
T
Yoshino
H
H
Satoh
N
N
Murakami
K
K
Patra
D
D
Iwata
C
C
Maezaki
N
N
Tanaka
T
T
D000998:Antiviral Agents / Q000138:chemical synthesis*; D004224:Diterpenes / Q000138:chemical synthesis*; D008745:Methylation; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D004224:Diterpenes; C064856:scopadulin