Radical cyclization of β-aminoacrylates: Synthesis of (-)-indolizidine 223AB

Organic Letters

Volumn 2, Issue 14, 2000, Pages 2169-2171

  Lee, Eun ^a   Jeong, Eun Jeong ^a   Min, Sun Joon ^a   Hong, Sukwon ^a   Lim, Jaehong ^a   Kim, Sang Kyun ^a   Kim, Hak Joong ^a   Choi, Bum Gyu ^a   Koo, Ki Chul ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INDOLE DERIVATIVE; INDOLIZIDINE 223AB; INDOLIZINE DERIVATIVE;

ANIMAL; ARTICLE; CHEMISTRY; CYCLIZATION; FROGS AND TOADS; METABOLISM; SKIN; SYNTHESIS;

ANIMALS; ANURA; CYCLIZATION; INDICATORS AND REAGENTS; INDOLES; INDOLIZINES; SKIN;

EID: 0034644006     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006094z     Document Type: Article

References (33)

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10. For further developments, see the following references. (a) Use of acyl radicals: Evans, P. A.; Roseman, J. D.; Garber, L. T. J. Org. Chem. 1996, 61, 4880, and the references therein.
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19. Cyclization products were not obtained from p-toluenesulfonamide substrates, which were mainly recovered.
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22. A ∼4:1 mixture of E/Z geometric isomers was obtained, and the mixture was directly used in the radical cyclization reaction.
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25. Only E isomers were obtained.
26. D = -100 (c 0.5, n-hexane).
27. For synthesis of (-)-indolizidine 223AB, see the following references; for synthesis of the racemic mixture, check the references therein. (a) Royer, J.; Husson, H.-P. Tetrahedron Lett. 1985, 26, 1515.
28. (b) The ref 6.
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33. Using the methyl ester analogue of 17, methyl ester analogues of 22/23 (23%, 4.9:1, stereochemistry unknown) and 24 (60%) were obtained.