Literature DB >> 17511508

Indole diterpene synthetic studies: development of a second-generation synthetic strategy for (+)-nodulisporic acids A and B.

Amos B Smith1, László Kürti, Akin H Davulcu, Young Shin Cho, Kazuyuki Ohmoto.   

Abstract

A second-generation strategy for construction of (+)-nodulisporic acids A and B based on the development of a new, effective modular indole synthesis exploiting a sequential Stille cross-coupling/Buchwald-Hartwig union/cyclization tactic is disclosed. This strategy evolved due to the considerable acid instability of the C(24) hydroxyl group observed in several advanced intermediates during our first-generation approach.

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Year:  2007        PMID: 17511508     DOI: 10.1021/jo062423a

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  11 in total

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

Authors:  Yike Zou; Xiangqin Li; Yun Yang; Simon Berritt; Jason Melvin; Stephen Gonzales; Matthew Spafford; Amos B Smith
Journal:  J Am Chem Soc       Date:  2018-07-20       Impact factor: 15.419

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

Authors:  Nicole A Godfrey; Devon J Schatz; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2018-09-28       Impact factor: 15.419

3.  A global and local desymmetrization approach to the synthesis of steroidal alkaloids: stereocontrolled total synthesis of paspaline.

Authors:  Robert J Sharpe; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2015-04-09       Impact factor: 15.419

4.  Application of 6,7-indole aryne cycloaddition and Pd(0)-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions for the preparation of annulated indole libraries.

Authors:  Paul D Thornton; Neil Brown; David Hill; Ben Neuenswander; Gerald H Lushington; Conrad Santini; Keith R Buszek
Journal:  ACS Comb Sci       Date:  2011-06-30       Impact factor: 3.784

5.  Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling.

Authors:  Nalin Chandrasoma; Neil Brown; Allen Brassfield; Alok Nerurkar; Susana Suarez; Keith R Buszek
Journal:  Tetrahedron Lett       Date:  2013-02-20       Impact factor: 2.415

6.  Total Synthesis of (-)-Nodulisporic Acid D.

Authors:  Yike Zou; Jason E Melvin; Stephen S Gonzales; Matthew J Spafford; Amos B Smith
Journal:  J Am Chem Soc       Date:  2015-06-01       Impact factor: 15.419

7.  Experimental and theoretical investigations into the unusual regioselectivity of 4,5-, 5,6-, and 6,7-indole aryne cycloadditions.

Authors:  Ashley N Garr; Diheng Luo; Neil Brown; Christopher J Cramer; Keith R Buszek; David VanderVelde
Journal:  Org Lett       Date:  2010-01-01       Impact factor: 6.005

8.  Catalytic Atroposelective C7 Functionalisation of Indolines and Indoles.

Authors:  Saad Shaaban; Christian Merten; Herbert Waldmann
Journal:  Chemistry       Date:  2021-11-05       Impact factor: 5.020

9.  Study on the synthesis of the cyclopenta[f]indole core of raputindole A.

Authors:  Nils Marsch; Mario Kock; Thomas Lindel
Journal:  Beilstein J Org Chem       Date:  2016-02-23       Impact factor: 2.883

10.  4-Methyltetrahydropyran (4-MeTHP): Application as an Organic Reaction Solvent.

Authors:  Shoji Kobayashi; Tomoki Tamura; Saki Yoshimoto; Takashi Kawakami; Araki Masuyama
Journal:  Chem Asian J       Date:  2019-10-16
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