Efficient total syntheses of phytoalexin and (+/-)-paniculidine B and C based on the novel methodology for the preparation of 1-methoxyindoles.
A general route to 2-unsubstituted-1-methoxyindoles, based on our methodology for the synthesis of 1-methoxyindoles, is reported. This synthesis renders accessibility to a variety of natural products possessing the said skeleton. A direct synthesis of phytoalexin (1), (+/-)-paniculidine B (2), and (+/-)-paniculidine C (3) is disclosed based on the methodology. The synthesis of paniculidine B (2) has been achieved from aldehyde 10 in only two steps in 88% yield and in five steps from a methoxyindole compound 8 obtained using our earlier methodology.
Selvakumar
N
N
Department of Discovery Chemistry, Discovery Research, Dr. Reddy's Laboratories Ltd, Miyapur, Hyderabad 500 049, India. selvakumarn@drreddys.com
Rajulu
G Govinda
GG
D007211:Indoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010936:Plant Extracts / Q000138:chemical synthesis*; D012717:Sesquiterpenes; D013729:Terpenes; D000094162:Phytoalexins
D007211:Indoles; D010936:Plant Extracts; D012717:Sesquiterpenes; D013729:Terpenes; C499196:paniculidine B; C499197:paniculidine C; D000094162:Phytoalexins