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Literature DB >> 30028603

Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.

Yike Zou¹, Xiangqin Li¹, Yun Yang¹, Simon Berritt¹, Jason Melvin¹, Stephen Gonzales¹, Matthew Spafford¹, Amos B Smith¹.

Abstract

A unified synthetic strategy leading to the total synthesis of (-)-nodulisporic acids D, C, and B is described. Key synthetic transformations include a nickel-chromium-mediated cyclization, an aromatic ring functionalization employing a novel copper-promoted alkylation, a palladium-catalyzed cross-coupling cascade/indole ring construction, and a palladium-mediated regio- and diastereoselective allylic substitution/cyclization reaction, the latter to construct ring D.

Entities: CellLine Chemical Disease Species

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Year: 2018 PMID： 30028603 PMCID： PMC6085755 DOI： 10.1021/jacs.8b04053

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

41 in total

1. Nodulisporic acids C, C1, and C2: a series of D-ring-opened nodulisporic acids from the fungus Nodulisporium sp.

Authors: John G Ondeyka; Kevin Byrne; Diane Vesey; Deborah L Zink; Wesley L Shoop; Michael A Goetz; Sheo B Singh
Journal: J Nat Prod Date: 2003-01 Impact factor: 4.050

2. New air-stable catalysts for general and efficient suzuki-miyaura cross-coupling reactions of heteroaryl chlorides.

Authors: Anil S Guram; Anthony O King; John G Allen; Xianghong Wang; Laurie B Schenkel; Johann Chan; Emilio E Bunel; Margaret M Faul; Robert D Larsen; Michael J Martinelli; Paul J Reider
Journal: Org Lett Date: 2006-04-27 Impact factor: 6.005

3. An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Authors: Jun Pan; Xinyan Wang; Yong Zhang; Stephen L Buchwald
Journal: Org Lett Date: 2011-08-24 Impact factor: 6.005

4. Nodulisporic acid A synthetic studies. 1. Overall strategy and construction of a western hemisphere subtarget.

Authors: A B Smith; H Ishiyama; Y S Cho; K Ohmoto
Journal: Org Lett Date: 2001-11-29 Impact factor: 6.005

5. An Efficient Protocol for the Oxidative Hydrolysis of Ketone SAMP Hydrazones Employing SeO(2) and H(2)O(2) under Buffered (pH 7) Conditions.

Authors: Amos B Smith; Zhuqing Liu; Vladimir Simov
Journal: Synlett Date: 2009-06 Impact factor: 2.454

6. Indole diterpenoid synthetic studies. The total synthesis of (+)-nodulisporic acid F.

Authors: Amos B Smith; Akin H Davulcu; Laszló Kürti
Journal: Org Lett Date: 2006-04-13 Impact factor: 6.005

7. Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Authors: Xiaoqiang Shen; Alan M Hyde; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419

8. A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors: Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419

9. New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: controlling the regioselectivity.

Authors: Marco Bandini; Alfonso Melloni; Achille Umani-Ronchi
Journal: Org Lett Date: 2004-09-02 Impact factor: 6.005

Total Synthesis of (-)-Nodulisporic Acids D, C, and B: Evolution of a Unified Synthetic Strategy.

1. Nodulisporic acids C, C1, and C2: a series of D-ring-opened nodulisporic acids from the fungus Nodulisporium sp.

2. New air-stable catalysts for general and efficient suzuki-miyaura cross-coupling reactions of heteroaryl chlorides.

3. An improved palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

4. Nodulisporic acid A synthetic studies. 1. Overall strategy and construction of a western hemisphere subtarget.

5. An Efficient Protocol for the Oxidative Hydrolysis of Ketone SAMP Hydrazones Employing SeO(2) and H(2)O(2) under Buffered (pH 7) Conditions.

6. Indole diterpenoid synthetic studies. The total synthesis of (+)-nodulisporic acid F.

7. Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

8. A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

9. New versatile Pd-catalyzed alkylation of indoles via nucleophilic allylic substitution: controlling the regioselectivity.

10. Iridium-catalyzed regio- and enantioselective N-allylation of indoles.

1. Recent Progress in Steroid Synthesis Triggered by the Emergence of New Catalytic Methods.

2. Twelve-Step Asymmetric Synthesis of (-)-Nodulisporic Acid C.

3. Late-Stage Diversification: A Motivating Force in Organic Synthesis.

4. Total Synthesis of Mycinamicin IV as Integral Part of a Collective Approach to Macrolide Antibiotics.

5. Total Synthesis of Shearinines D and G: A Convergent Approach to Indole Diterpenoids.