Literature DB >> 30261724

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

Nicole A Godfrey1, Devon J Schatz1, Sergey V Pronin1.   

Abstract

A short, enantioselective synthesis of (-)-nodulisporic acid C is described. The route features two highly diastereoselective polycyclizations en route to the terpenoid core and the indenopyran fragment and a highly convergent assembly of a challenging indole moiety. Application of this chemistry allows for a 12-step synthesis of the target indoloterpenoid from commercially available material.

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Year:  2018        PMID： 30261724      PMCID： PMC6791361          DOI： 10.1021/jacs.8b09965

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


  45 in total

1.  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
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2.  Synthesis of (±)-terpendole E.

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3.  A new modular indole synthesis. Construction of the highly strained CDEF parent tetracycle of nodulisporic acids A and B.

Authors:  Amos B Smith; Laszló Kürti; Akin H Davulcu
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

4.  Nodulisporic acids D-F: structure, biological activities, and biogenetic relationships.

Authors:  Sheo B Singh; John G Ondeyka; Hiranthi Jayasuriya; Deborah L Zink; Sookhee N Ha; Arlene Dahl-Roshak; Joyce Greene; Jennifer A Kim; McHardy M Smith; Wesley Shoop; Jan S Tkacz
Journal:  J Nat Prod       Date:  2004-09       Impact factor: 4.050

5.  A Concise Approach to Paxilline Indole Diterpenes.

Authors:  David T George; Eric J Kuenstner; Sergey V Pronin
Journal:  J Am Chem Soc       Date:  2015-12-07       Impact factor: 15.419

6.  Biosynthesis of nodulisporic acid A: precursor studies.

Authors:  Kevin M Byrne; Scott K Smith; John G Ondeyka
Journal:  J Am Chem Soc       Date:  2002-06-19       Impact factor: 15.419

7.  Indole diterpene synthetic studies. Total synthesis of (+)-nodulisporic acid F and construction of the heptacyclic cores of (+)-nodulisporic acids A and B and (-)-nodulisporic acid D.

Authors:  Amos B Smith; Akin H Davulcu; Young Shin Cho; Kazuyuki Ohmoto; László Kürti; Haruaki Ishiyama
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9.  Fe-Catalyzed C-C Bond Construction from Olefins via Radicals.

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Review 10.  Indole diterpenoid natural products as the inspiration for new synthetic methods and strategies.

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Journal:  Chem Sci       Date:  2017-06-27       Impact factor: 9.825
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Review 5.  Reductive radical-polar crossover: traditional electrophiles in modern radical reactions.

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Journal:  Chem Sci       Date:  2019-08-16       Impact factor: 9.825

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

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Review 7.  Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances.

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  7 in total

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