Literature DB >> 17691801

First total synthesis and structural reassignment of (-)-aplysiallene.

Jian Wang1, Brian L Pagenkopf.   

Abstract

The first total synthesis of (-)-aplysiallene has been completed in 16 steps and features a key sequential Mukaiyama aerobic oxidative cyclization to prepare the fused bis-THF core. The original stereochemical assignment has been revised as shown.

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Year:  2007        PMID： 17691801     DOI： 10.1021/ol701797e

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


  10 in total

Review 1.  Survey of marine natural product structure revisions: a synergy of spectroscopy and chemical synthesis.

Authors:  Takashi L Suyama; William H Gerwick; Kerry L McPhail
Journal:  Bioorg Med Chem       Date:  2011-06-12       Impact factor: 3.641

2.  An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.

Authors:  Sudeshna Roy; Christopher D Spilling
Journal:  Org Lett       Date:  2012-04-16       Impact factor: 6.005

3.  Allylic and allenic halide synthesis via NbCl(5)- and NbBr(5)-mediated alkoxide rearrangements.

Authors:  P C Ravikumar; Lihua Yao; Fraser F Fleming
Journal:  J Org Chem       Date:  2009-10-02       Impact factor: 4.354

4.  Synthesis of fused-ring and attached-ring bis-tetrahydrofurans via Pd-catalyzed carboetherification.

Authors:  Amanda F Ward; John P Wolfe
Journal:  Org Lett       Date:  2009-05-21       Impact factor: 6.005

Review 5.  Stereoselective Halogenation in Natural Product Synthesis.

Authors:  Won-jin Chung; Christopher D Vanderwal
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

Review 6.  Chemical Diversity and Biological Properties of Secondary Metabolites from Sea Hares of Aplysia Genus.

Authors:  Renato B Pereira; Paula B Andrade; Patrícia Valentão
Journal:  Mar Drugs       Date:  2016-02-19       Impact factor: 5.118

Review 7.  The direct oxidative diene cyclization and related reactions in natural product synthesis.

Authors:  Juliane Adrian; Leona J Gross; Christian B W Stark
Journal:  Beilstein J Org Chem       Date:  2016-09-30       Impact factor: 2.883

8.  Total synthesis and complete configurational assignment of amphirionin-2.

Authors:  Shota Kato; Daichi Mizukami; Tomoya Sugai; Masashi Tsuda; Haruhiko Fuwa
Journal:  Chem Sci       Date:  2020-11-20       Impact factor: 9.825

9.  Forwards and backwards - synthesis of Laurencia natural products using a biomimetic and retrobiomimetic strategy incorporating structural reassignment of laurefurenynes C-F.

Authors:  Hau Sun Sam Chan; Amber L Thompson; Kirsten E Christensen; Jonathan W Burton
Journal:  Chem Sci       Date:  2020-10-08       Impact factor: 9.825

Review 10.  Marine Invertebrate Metabolites with Anticancer Activities: Solutions to the "Supply Problem".

Authors:  Nelson G M Gomes; Ramesh Dasari; Sunena Chandra; Robert Kiss; Alexander Kornienko
Journal:  Mar Drugs       Date:  2016-05-21       Impact factor: 5.118
  10 in total

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