Indole diterpene synthetic studies: development of a second-generation synthetic strategy for (+)-nodulisporic acids A and B.
A second-generation strategy for construction of (+)-nodulisporic acids A and B based on the development of a new, effective modular indole synthesis exploiting a sequential Stille cross-coupling/Buchwald-Hartwig union/cyclization tactic is disclosed. This strategy evolved due to the considerable acid instability of the C(24) hydroxyl group observed in several advanced intermediates during our first-generation approach.
Smith
Amos B
AB
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Kürti
László
L
Davulcu
Akin H
AH
Cho
Young Shin
YS
Ohmoto
Kazuyuki
K
D000586:Amination; D000814:Aniline Compounds / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D007783:Lactones / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013816:Thermodynamics
D000814:Aniline Compounds; D004224:Diterpenes; D007211:Indoles; D007783:Lactones; C471907:nodulisporic acid B; C110703:nodulisporic acid A; C023650:aniline