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Literature DB >> 22214219

Synthetic studies toward lapidilectine-type Kopsia alkaloids.

Erica E Schultz¹, Brian G Pujanauski, Richmond Sarpong.

Abstract

A rapid synthesis of the tetracyclic core of Kopsia indole alkaloids related to lapidilectine B, grandilodine C, and tenuisine A is reported. Key to the success of this route was an efficient and scalable Ugi four-component coupling to install all the necessary carbons found in the natural products.

Entities: CellLine Chemical Disease Gene

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Year: 2012 PMID： 22214219 PMCID： PMC3262909 DOI： 10.1021/ol203302f

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

12 in total

1. Total synthesis of the Kopsia lapidilecta alkaloid (+/-)-lapidilectine B.

Authors: W H Pearson; Y Mi; I Y Lee; P Stoy
Journal: J Am Chem Soc Date: 2001-07-11 Impact factor: 15.419

2. Multicomponent Reactions with Isocyanides.

Authors:
Journal: Angew Chem Int Ed Engl Date: 2000-09-15 Impact factor: 15.336

3. A Synthesis of the Tricyclic Core Structure of FR901483 Featuring an Ugi Four-Component Coupling and a Remarkably Selective Elimination Reaction.

Authors: Hirofumi Seike; Erik J Sorensen
Journal: Synlett Date: 2008-03-18 Impact factor: 2.454

4. Intra- and intermolecular reactions of indoles with alkynes catalyzed by gold.

Authors: Catalina Ferrer; Catelijne H M Amijs; Antonio M Echavarren
Journal: Chemistry Date: 2007 Impact factor: 5.236

5. The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation.

Authors: John A Enquist; Brian M Stoltz
Journal: Nature Date: 2008-06-26 Impact factor: 49.962

6. Efficient synthesis of the indoloazocine framework via intramolecular alkyne carbocyclization.

Authors: Pavel A Donets; Kristof Van Hecke; Luc Van Meervelt; Erik V Van der Eycken
Journal: Org Lett Date: 2009-08-20 Impact factor: 6.005

7. Grandilodines A-C, biologically active indole alkaloids from Kopsia grandifolia.

Authors: Wai-Sum Yap; Chew-Yan Gan; Yun-Yee Low; Yeun-Mun Choo; Tadahiro Etoh; Masahiko Hayashi; Kanki Komiyama; Toh-Seok Kam
Journal: J Nat Prod Date: 2011-03-23 Impact factor: 4.050

8. Thiol-catalyzed acyl radical cyclization of alkenals.

Authors: Kazuya Yoshikai; Tomoharu Hayama; Katsumi Nishimura; Ken-Ichi Yamada; Kiyoshi Tomioka
Journal: J Org Chem Date: 2005-01-21 Impact factor: 4.354

9. Cyclobutanes in catalysis.

Authors: Tobias Seiser; Tanguy Saget; Duc N Tran; Nicolai Cramer
Journal: Angew Chem Int Ed Engl Date: 2011-07-26 Impact factor: 15.336

10. Synthesis of the tetracyclic core of the neomangicols using a late-stage indene alkylation.

Authors: Jessica L Wood; Brian G Pujanauski; Richmond Sarpong
Journal: Org Lett Date: 2009-07-16 Impact factor: 6.005

4 in total

1. Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-Lundurine A.

Authors: Aaron Nash; Xiangbing Qi; Pradip Maity; Kyle Owens; Uttam K Tambar
Journal: Angew Chem Int Ed Engl Date: 2018-05-04 Impact factor: 15.336

2. Concise Total Synthesis of Lundurines A-C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization.

Authors: Mariia S Kirillova; Michael E Muratore; Ruth Dorel; Antonio M Echavarren
Journal: J Am Chem Soc Date: 2016-03-15 Impact factor: 15.419

3. Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship.

Authors: Fedor M Miloserdov; Mariia S Kirillova; Michael E Muratore; Antonio M Echavarren
Journal: J Am Chem Soc Date: 2018-02-22 Impact factor: 15.419

4. Synthesis of indole-based propellane derivatives via Weiss-Cook condensation, Fischer indole cyclization, and ring-closing metathesis as key steps.

Authors: Sambasivarao Kotha; Ajay Kumar Chinnam; Arti Tiwari
Journal: Beilstein J Org Chem Date: 2013-11-29 Impact factor: 2.883

4 in total