Interrupted Fischer indolization approach toward the communesin alkaloids and perophoramidine.
A concise approach toward the total synthesis of the communesin alkaloids and perophoramidine is reported. The strategy relies on the use of the interrupted Fischer indolization to build the tetracyclic indoline core of the natural products. Studies to probe the scope and limitations of this plan are presented. Although the methodology does not tolerate a C8-allyl substituent en route to the challenging vicinal quaternary stereocenters, variation at C7 and on the C ring is permitted.
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.
Alex W
AW
Schammel
Grace
G
Chiou
Neil K
NK
Garg
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings; D006846:Hydrocarbons, Halogenated; C472225:perophoramidine