Literature DB >> 21062039

Diastereoselective syntheses of indoloquinolizidines by a Pictet-Spengler/lactamization cascade.

Huihui Fang1, Xiaoyu Wu, Linlin Nie, Xiaoyang Dai, Jie Chen, Weiguo Cao, Gang Zhao.   

Abstract

An expedient diastereoselective synthesis of highly functionalized indolo[2,3-α]quinolizidines adopting a cis H2/H12b geometry has been realized by a Pictet-Spengler/lactamization cascade sequence. The absolute stereochemistry at C2, C3, and C12b was governed by the originally created chirality of the Michael adduct through organocatalyzed conjugate addition of dialkyl malonates to α,β-unsaturated aldehydes.

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Year:  2010        PMID: 21062039     DOI: 10.1021/ol101922h

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


  6 in total

1.  Enantioselective Pictet-Spengler Reactions of Isatins for the Synthesis of Spiroindolones.

Authors:  Joseph J Badillo; Abel Silva-García; Benjamin H Shupe; James C Fettinger; Annaliese K Franz
Journal:  Tetrahedron Lett       Date:  2011-10-26       Impact factor: 2.415

Review 2.  The Chiral Pool in the Pictet-Spengler Reaction for the Synthesis of β-Carbolines.

Authors:  Renato Dalpozzo
Journal:  Molecules       Date:  2016-05-27       Impact factor: 4.411

3.  Aza-Annulation of 1,2,3,4-Tetrahydro-β-carboline Derived Enaminones and Nitroenamines: Synthesis of Functionalized Indolizino[8,7-b]indoles, Pyrido[1,2-a:3,4-b']diindoles, Indolo[2,3-a]quinolizidine-4-ones and Other Tetrahydro-β-carboline Fused Heterocycles.

Authors:  Anusha Avadhani; Pethaperumal Iniyavan; Anand Acharya; Vibha Gautam; Sriparna Chakrabarti; Hiriyakkanavar Ila
Journal:  ACS Omega       Date:  2019-10-16

4.  Convenient construction of tetrahydrochromeno[4',3':2,3]indolizino[8,7-b]indoles and tetrahydroindolizino[8,7-b]indoles via one-pot domino reaction.

Authors:  Jing Sun; Wang Jiang; Chao-Guo Yan
Journal:  RSC Adv       Date:  2018-08-14       Impact factor: 3.361

5.  Mechanistic study of the spiroindolones: a new class of antimalarials.

Authors:  Bin Zou; Peiling Yap; Louis-Sebastian Sonntag; Seh Yong Leong; Bryan K S Yeung; Thomas H Keller
Journal:  Molecules       Date:  2012-08-24       Impact factor: 4.411

Review 6.  The Pictet-Spengler Reaction Updates Its Habits.

Authors:  Andrea Calcaterra; Laura Mangiardi; Giuliano Delle Monache; Deborah Quaglio; Silvia Balducci; Simone Berardozzi; Antonia Iazzetti; Roberta Franzini; Bruno Botta; Francesca Ghirga
Journal:  Molecules       Date:  2020-01-19       Impact factor: 4.411

  6 in total

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