Literature DB >> 23627293

Synthesis of a highly functionalized core of verrillin.

Alec Saitman1, Emmanuel A Theodorakis.   

Abstract

An efficient stereoselective synthesis of furanoverrillin (5), a highly functionalized core of verrillin (1), is reported. The synthetic strategy is based on constructing bicyclic lactone 17 prior to the 10-membered ring macrocyclization. The effect of the C4 methyl group on the furan reactivity is also discussed.

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Year:  2013        PMID： 23627293      PMCID： PMC3766406          DOI： 10.1021/ol400872h

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


  24 in total

1.  Exploring biosynthetic relationships among furanocembranoids: synthesis of (-)-bipinnatin J, (+)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B.

Authors:  Paul A Roethle; Paul T Hernandez; Dirk Trauner
Journal:  Org Lett       Date:  2006-12-07       Impact factor: 6.005

Review 2.  Metabolites from Sinularia species.

Authors:  V Lakshmi; R Kumar
Journal:  Nat Prod Res       Date:  2009       Impact factor: 2.861

Review 3.  The chemistry of marine furanocembranoids, pseudopteranes, gersolanes, and related natural products.

Authors:  Paul A Roethle; Dirk Trauner
Journal:  Nat Prod Rep       Date:  2008-02-25       Impact factor: 13.423

4.  Gold catalysis: non-spirocyclic intermediates in the conversion of furanynes by the formal insertion of an alkyne into an aryl-alkyl C-C single bond.

Authors:  A Stephen K Hashmi; Tobias Häffner; Weibo Yang; Sreekumar Pankajakshan; Sascha Schäfer; Lara Schultes; Frank Rominger; Wolfgang Frey
Journal:  Chemistry       Date:  2012-07-16       Impact factor: 5.236

5.  A strategy toward the synthesis of C13-oxidized cembrenolides.

Authors:  Alec Saitman; Steven D E Sullivan; Emmanuel A Theodorakis
Journal:  Tetrahedron Lett       Date:  2013-03-20       Impact factor: 2.415

6.  Total synthesis of norcembrenolide B and scabrolide D.

Authors:  Alec Saitman; Pauline Rulliere; Steven D E Sullivan; Emmanuel A Theodorakis
Journal:  Org Lett       Date:  2011-10-05       Impact factor: 6.005

7.  Expedient synthesis of (+/-)-bipinnatin J.

Authors:  Paul A Roethle; Dirk Trauner
Journal:  Org Lett       Date:  2006-01-19       Impact factor: 6.005

8.  Synthesis of a lactone diastereomer of the cembranolide uprolide D.

Authors:  James A Marshall; Céline A Griot; Harry R Chobanian; William H Myers
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

9.  Evidence for a carbocation intermediate during conversion of bipinnatin-A and -C into irreversible inhibitors of nicotinic acetylcholine receptors.

Authors:  E G Hyde; S M Thornhill; A J Boyer; S N Abramson
Journal:  J Med Chem       Date:  1995-11-10       Impact factor: 7.446

10.  A non-photochemical approach to the bicyclo[3.2.0]heptane core of bielschowskysin.

Authors:  Jean-Baptiste Farcet; Martin Himmelbauer; Johann Mulzer
Journal:  Org Lett       Date:  2012-04-16       Impact factor: 6.005
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  5 in total

Review 1.  Polycyclic Furanobutenolide-Derived Cembranoid and Norcembranoid Natural Products: Biosynthetic Connections and Synthetic Efforts.

Authors:  Robert A Craig; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-05-18       Impact factor: 60.622

2.  Synthesis of Agelastatin A and Derivatives Premised on a Hidden Symmetry Element Leading to Analogs Displaying Anticancer Activity.

Authors:  Haoran Xue; Haleigh Svatek; Ariane F Bertonha; Keighley Reisenauer; Joshua Robinson; Minwoo Kim; Alec Ingros; Matthew Ho; Joseph Taube; Daniel Romo
Journal:  Tetrahedron       Date:  2021-07-10       Impact factor: 2.388

3.  Synthetic Strategies Toward the Decalin Motif of Maklamicin and Related Spirotetronates.

Authors:  Michelle H Lacoske; Jing Xu; Noel Mansour; Chao Gao; Emmanuel A Theodorakis
Journal:  Org Chem Front       Date:  2015-04-01       Impact factor: 5.281

4.  Pharmacophore-Directed Retrosynthesis Applied to Rameswaralide: Synthesis and Bioactivity of Sinularia Natural Product Tricyclic Cores.

Authors:  Nathanyal J Truax; Safiat Ayinde; Khoi Van; Jun O Liu; Daniel Romo
Journal:  Org Lett       Date:  2019-09-09       Impact factor: 6.005

Review 5.  Catalytic enantioselective synthesis of chiral organic compounds of ultra-high purity of >99% ee.

Authors:  Ei-ichi Negishi; Shiqing Xu
Journal:  Proc Jpn Acad Ser B Phys Biol Sci       Date:  2015       Impact factor: 3.493
  5 in total

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