Literature DB >> 26485318

Construction of Enantiopure Taxoid and Natural Product-like Scaffolds Using a C-C Bond Cleavage/Arylation Reaction.

Manuel Weber1, Kyle Owens1, Ahmad Masarwa1, Richmond Sarpong1.   

Abstract

An approach to construct enantiopure complex natural product-like frameworks, including the first reported synthesis of a C17 oxygenated taxoid scaffold, is presented. A palladium-catalyzed C-C activation/cross-coupling is utilized to access these structures in a short sequence from (+)-carvone; the scope of this reaction is explored.

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Year:  2015        PMID： 26485318     DOI： 10.1021/acs.orglett.5b02797

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


  11 in total

Review 1.  Transition Metal-Mediated C-C Single Bond Cleavage: Making the Cut in Total Synthesis.

Authors:  Brian Wang; Melecio A Perea; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-24       Impact factor: 15.336

Review 2.  Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.

Authors:  Zachary G Brill; Matthew L Condakes; Chi P Ting; Thomas J Maimone
Journal:  Chem Rev       Date:  2017-03-15       Impact factor: 60.622

3.  Total Syntheses of Xiamycins A, C, F, H and Oridamycin A and Preliminary Evaluation of their Anti-Fungal Properties.

Authors:  Magnus Pfaffenbach; Ian Bakanas; Nicholas R O'Connor; Jessica L Herrick; Richmond Sarpong
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-12       Impact factor: 15.336

4.  Total synthesis of nine longiborneol sesquiterpenoids using a functionalized camphor strategy.

Authors:  Robert F Lusi; Goh Sennari; Richmond Sarpong
Journal:  Nat Chem       Date:  2022-02-14       Impact factor: 24.274

5.  Rearrangements of the Chrysanthenol Core: Application to a Formal Synthesis of Xishacorene B.

Authors:  Kerry E Jones; Bohyun Park; Nicolle A Doering; Mu-Hyun Baik; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2021-11-23       Impact factor: 16.383

6.  Access to a Structurally Complex Compound Collection via Ring Distortion of the Alkaloid Sinomenine.

Authors:  Alfredo Garcia; Bryon S Drown; Paul J Hergenrother
Journal:  Org Lett       Date:  2016-09-21       Impact factor: 6.005

7.  C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins.

Authors:  Paul R Leger; Yusuke Kuroda; Stanley Chang; Justin Jurczyk; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2020-08-31       Impact factor: 15.419

8.  Limonin as a Starting Point for the Construction of Compounds with High Scaffold Diversity.

Authors:  Lucia Furiassi; Emily J Tonogai; Paul J Hergenrother
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-10       Impact factor: 16.823

9.  Synthesis and Demonstration of the Biological Relevance of sp3 -rich Scaffolds Distantly Related to Natural Product Frameworks.

Authors:  Daniel J Foley; Philip G E Craven; Patrick M Collins; Richard G Doveston; Anthony Aimon; Romain Talon; Ian Churcher; Frank von Delft; Stephen P Marsden; Adam Nelson
Journal:  Chemistry       Date:  2017-10-06       Impact factor: 5.236

10.  Bio-inspired synthesis of xishacorenes A, B, and C, and a new congener from fuscol.

Authors:  Alexander R Rovira; Nicolas Müller; Weiwen Deng; Chudi Ndubaku; Richmond Sarpong
Journal:  Chem Sci       Date:  2019-07-03       Impact factor: 9.825
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