Progress toward the total synthesis of saudin: development of a tandem Stille-oxa-electrocyclization reaction.
[reaction: see text] A diastereoselective tandem Stille-oxa-electrocyclization reaction provides access to the core of the diterpenoid natural product saudin. Additionally, this new reaction sequence was extended to the convergent preparation of related polycyclic pyran systems.
Tambar
Uttam K
UK
The Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Kano
Taichi
T
Stoltz
Brian M
BM
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011084:Polycyclic Aromatic Hydrocarbons / Q000138:chemical synthesis*; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
D004224:Diterpenes; D005663:Furans; D011084:Polycyclic Aromatic Hydrocarbons; D011714:Pyrans; C450680:saudin