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Literature DB >> 29066790

Challenges and discoveries in the total synthesis of complex polyketide natural products.

Abstract

Structurally complex polyketide natural products, isolated from a variety of marine and terrestrial sources, continue to provide a valuable source of rewarding targets for the synthetic chemist to tackle. In this account, we provide an overview of the total synthesis of several structurally fascinating polyketides with promising anticancer activity completed in our group based on our versatile asymmetric aldol methodology-spirastrellolide A methyl ester, leiodermatolide, rhizopodin and chivosazole F-and highlight the unanticipated challenges and discoveries encountered.

Entities: Chemical

Mesh：

Substances：

Year: 2017 PMID： 29066790 DOI： 10.1038/ja.2017.111

Source DB: PubMed Journal: J Antibiot (Tokyo) ISSN： 0021-8820 Impact factor: 2.649

66 in total

1. Synthesis of the C9-C23 (C9'-C23') fragment of the dimeric natural product rhizopodin.

Authors: Zheng Chen; Liankai Song; Zhengshuang Xu; Tao Ye
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

2. Chemistry. The renaissance of natural products as drug candidates.

Authors: Ian Paterson; Edward A Anderson
Journal: Science Date: 2005-10-21 Impact factor: 47.728

3. Spirastrellolide B reveals the absolute configuration of the spirastrellolide macrolide core.

Authors: Kaoru Warabi; David E Williams; Brian O Patrick; Michel Roberge; Raymond J Andersen
Journal: J Am Chem Soc Date: 2007-01-24 Impact factor: 15.419

4. Diastereo- and Enantioselective Synthesis of syn-alpha-Vinylchlorohydrins and cis-Vinylepoxides.

Authors: Shaojing Hu; Seetharaman Jayaraman; Allan C. Oehlschlager
Journal: J Org Chem Date: 1996-10-18 Impact factor: 4.354

5. Stereoselective synthesis of the monomeric unit of actin binding macrolide rhizopodin.

Authors: Kiran Kumar Pulukuri; Tushar Kanti Chakraborty
Journal: Org Lett Date: 2012-05-18 Impact factor: 6.005

6. Synthesis of the macrocyclic core of leiodermatolide.

Authors: Ian Paterson; Tanya Paquet; Stephen M Dalby
Journal: Org Lett Date: 2011-07-14 Impact factor: 6.005

7. Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

Authors: Adam F Littke; Lothar Schwarz; Gregory C Fu
Journal: J Am Chem Soc Date: 2002-06-05 Impact factor: 15.419

8. Synthesis of the C1-C13 tetraenoate subunit of the chivosazoles.

Authors: Ian Paterson; S B Jennifer Kan; Lisa J Gibson
Journal: Org Lett Date: 2010-08-20 Impact factor: 6.005

9. Total synthesis of (+)-discodermolide: an improved endgame exploiting a Still-Gennari-type olefination with a C1-C8 beta-ketophosphonate fragment.

Authors: Ian Paterson; Isabelle Lyothier
Journal: Org Lett Date: 2004-12-23 Impact factor: 6.005

10. Spirastrellolide A, an antimitotic macrolide isolated from the Caribbean marine sponge Spirastrella coccinea.

Authors: David E Williams; Michel Roberge; Rob Van Soest; Raymond J Andersen
Journal: J Am Chem Soc Date: 2003-05-07 Impact factor: 15.419

5 in total

1. Unusual Rearrangement-Remercuration Reactions of Allylic Silanols.

Authors: Someshwar Nagamalla; Ranjeet A Dhokale; Frederick J Seidl; Joel T Mague; Shyam Sathyamoorthi
Journal: Org Chem Front Date: 2021-08-03 Impact factor: 5.456

2. Divergent Asymmetric Synthesis of Panowamycins, TM-135, and Veramycin F Using C-H Insertion with Donor/Donor Carbenes.

Authors: Benjamin D Bergstrom; Amy T Merrill; James C Fettinger; Dean J Tantillo; Jared T Shaw
Journal: Angew Chem Int Ed Engl Date: 2022-04-25 Impact factor: 16.823