Literature DB >> 16597103

Total synthesis of ent-dihydrocorynantheol by using a proline-catalyzed asymmetric addition reaction.

Takashi Itoh1, Masashi Yokoya, Keiko Miyauchi, Kazuhiro Nagata, Akio Ohsawa.   

Abstract

[reaction: see text] 9-Tosyl-3,4-dihydro-beta-carboline reacted with 3-ethyl-3-buten-2-one in the presence of (S)-proline to give (3R,12bR)-3-ethyl-12-tosyl-3,4,6,7,8,9,10,11,12,12b-decahydro-1H-indolo[2,3-a]quinolizin-2-one in complete enantio- and diastereoselectivity. The compound thus obtained was readily transformed to ent-dihydrocorynantheol in three steps.

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Year:  2006        PMID： 16597103     DOI： 10.1021/ol0530575

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

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6.  Redox-Annulation of Cyclic Amines and β-Ketoaldehydes.

Authors:  Weijie Chen; Daniel Seidel
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Authors:  Xiaoxiao Song; Qijian Ni; Chen Zhu; Gerhard Raabe; Dieter Enders
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Journal:  Beilstein J Org Chem       Date:  2012-10-09       Impact factor: 2.883

9.  Asymmetric Redox-Annulation of Cyclic Amines.

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Journal:  J Org Chem       Date:  2015-10-02       Impact factor: 4.354

10.  Oxidative Asymmetric Formal Aza-Diels⁻Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones.

Authors:  Xiang Wu; Shi-Bao Zhao; Lang-Lang Zheng; You-Gui Li
Journal:  Molecules       Date:  2018-09-01       Impact factor: 4.411
  10 in total

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