Synthesis of (±)-pseudoheliotridane by allylboration of 1-pyrroline |
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| Authors: | M E Gurskii T V Potapova Yu N Bubnov |
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| Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation |
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| Abstract: | Reaction of tricrotylborane with 1-pyrroline proceeds stereoselectively to give (1R
*
,1′S
*
)-2-(1-methylallyl)pyrrolidine. The latter was converted to the pyrrolizidine alkaloid (±)-pseudoheliotridane through hydroboration-oxidation-intramolecular
cyclization.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1450–1452, July, 1998. |
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| Keywords: | pyrrolizidine alkaloids (±)-pseudoheliotridane allylboration stereochemistry tricrotylborane 1-pyrroline |
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