Tetrahedron p. 6173 - 6180 (1994)
Update date:2022-07-29
Topics:
Yerxa, Benjamin R.
Yang, Kevin
Moore, Harold W.
The total synthesis of the indolizidine alkaloid, (±)-septicine (5) (27% overall yield) in 8 steps from dimethyl squarate is presented. The key step of the synthesis involves the ring expansion of 2,3-bis-(3,4-dimethoxyphenyl)-4-(1-pyrrolo)cyclobutenone 12 to the corresponding indolizine-5,8-dione 6. The synthesis is highly convergent and thus could be used for the synthesis of a variety of analogs.
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Doi:10.1246/cl.1994.1211
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(1964)