An Efficient Synthesis of Phenanthroindolizidine Core via Hetero Diels-Alder Reaction of In Situ Generated α-Allenylchalcogenoketenes With Cyclic Imines

Synthesis of phenanthroindolizidine core was efficiently achieved through a pathway involving hetero Diels-Alder reaction of α-allenylchalcogenoketenes, generated in situ by thermal [3,3] sigmatropic rearrangement of alkynyl propargyl sulfides or selenides, with cyclic imines and the subsequent iodi...

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Bibliographic Details
Published in:Natural product communications 2019-06, Vol.14 (6)
Main Authors: Shimada, Kazuaki, Suzuki, Mariko, Yahaba, Kohei, Aoyagi, Shigenobu, Takikawa, Yuji, Korenaga, Toshinobu
Format: Article
Language:English
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Summary:Synthesis of phenanthroindolizidine core was efficiently achieved through a pathway involving hetero Diels-Alder reaction of α-allenylchalcogenoketenes, generated in situ by thermal [3,3] sigmatropic rearrangement of alkynyl propargyl sulfides or selenides, with cyclic imines and the subsequent iodine-assisted photochemical cyclization.
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X19857489