Journal
TETRAHEDRON
Volume 88, Issue -, Pages -Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2021.132121
Keywords
Aldehydes; Amination; Asymmetric synthesis; Natural products; Tetrahydroisoquinolines
Categories
Funding
- Science and Engineering Research Board, Department of Science and Technology India [EMR/2017/000414]
- Council of Scientific and Industrial Research (India), New Delhi
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An enantioselective route has been developed for the synthesis of C-1 substituted tetrahydroisoquinoline natural products. Six different natural products were successfully synthesized from a single aldehyde using proline-catalyzed asymmetric alpha-hydrazination reaction. The highly enantioselective introduction of an amino group allowed for the synthesis of (-)-calycotomine, (-)-salsolidine, (-)-carnegine, (+)-homolaudanosine, (+)-homoprotoberberine and (thorn)-crispine A.
An enantioselective route towards the synthesis of C-1 substituted tetrahydroisoquinoline natural products is reported. Six different natural products are synthesized from a single aldehyde using prolinecatalyzed asymmetric alpha-hydrazination reaction as the key step. The highly enantioselective introduction of an amino group is exploited to synthesize (-)-calycotomine, (-)-salsolidine, (-)-carnegine, (+)-homolaudanosine, (+)-homoprotoberberine and (thorn)-crispine A. (C) 2021 Elsevier Ltd. All rights reserved.
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