Literature DB >> 18821767

Total synthesis of (+)-lepadin F.

Gang Li1, Richard P Hsung, Brian W Slafer, Irina K Sagamanova.   

Abstract

An enantioselective total synthesis of (+)-lepadin F is described. The synthetic sequence features an intermolecular aza-[3 + 3] annulation, homologation of a vinylogous amide via Eschenmoser's episulfide contraction, and a highly stereoselective hydrogenation essential for achieving the 1,3-anti relative stereochemistry at C2 and C8a.

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Year:  2008        PMID： 18821767      PMCID： PMC2662136          DOI： 10.1021/ol802068q

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


  32 in total

1.  Development of a stepwise [3 + 3] annelation to functionalized piperidines.

Authors:  Katharine M Goodenough; Piotr Raubo; Joseph P A Harrity
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

2.  A [3 + 3] annelation approach to tetrahydropyridines.

Authors:  Lisa C Pattenden; Robert A J Wybrow; Stephen A Smith; Joseph P A Harrity
Journal:  Org Lett       Date:  2006-07-06       Impact factor: 6.005

3.  Ring expansion of functionalized octahydroindoles to enantiopure cis-decahydroquinolines.

Authors:  Marisa Mena; Josep Bonjoch; Domingo Gomez Pardo; Janine Cossy
Journal:  J Org Chem       Date:  2006-08-04       Impact factor: 4.354

4.  Highly stereoselective formal

Authors: 
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

5.  A novel and highly stereoselective approach to aza-spirocycles. A short total synthesis of 2-epi-(+/-)-perhydrohistrionicotoxin and an unprecedented decarboxylation of 2-pyrones.

Authors:  Michael J McLaughlin; Richard P Hsung; Kevin P Cole; Juliet M Hahn; Jiashi Wang
Journal:  Org Lett       Date:  2002-06-13       Impact factor: 6.005

6.  Total syntheses of enantiomerically enriched R-(+)- and S-(-)-deplancheine.

Authors:  Nadiya Sydorenko; Craig A Zificsak; Aleksey I Gerasyuto; Richard P Hsung
Journal:  Org Biomol Chem       Date:  2005-04-25       Impact factor: 3.876

7.  Lepadins F-H, new cis-decahydroquinoline alkaloids from the Australian ascidian Aplidium tabascum.

Authors:  Rohan A Davis; Anthony R Carroll; Ronald J Quinn
Journal:  J Nat Prod       Date:  2002-04       Impact factor: 4.050

8.  A concise total synthesis of (-)-cylindricine C through a stereoselective intramolecular aza-[3 + 3] annulation strategy.

Authors:  Jacob J Swidorski; Jiashi Wang; Richard P Hsung
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005

9.  Intramolecular formal aza-[3 + 3] cycloaddition approach to indoloquinolizidine alkaloids. A stereoselective total synthesis of (+/-)-tangutorine.

Authors:  Shengjun Luo; Craig A Zificsak; Richard P Hsung
Journal:  Org Lett       Date:  2003-11-27       Impact factor: 6.005

10.  Stereoselective formal [3 + 3] cycloaddition approach to cis-1-azadecalins and synthesis of (-)-4a,8a-diepi-pumiliotoxin C. evidence for the first highly stereoselective 6pi-electron electrocyclic ring closures of 1-azatrienes.

Authors:  Heather M Sklenicka; Richard P Hsung; Michael J McLaughlin; Lin-Li Wei; Aleksey I Gerasyuto; William B Brennessel
Journal:  J Am Chem Soc       Date:  2002-09-04       Impact factor: 15.419
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  7 in total

1.  Total synthesis of jadomycin A and a carbasugar analogue of jadomycin B.

Authors:  Mingde Shan; Ehesan U Sharif; George A O'Doherty
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-03       Impact factor: 15.336

2.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

3.  A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.

Authors:  Gang Li; Lauren J Carlson; Irina K Sagamanova; Brian W Slafer; Richard P Hsung; Claudio Gilardi; Heather M Sklenicka; Nadiya Sydroenko
Journal:  Synthesis (Stuttg)       Date:  2009-09-01       Impact factor: 3.157

4.  Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.

Authors:  Grant S Buchanan; Huifang Dai; Richard P Hsung; Aleksey I Gerasyuto; Casi M Scheinebeck
Journal:  Org Lett       Date:  2011-07-25       Impact factor: 6.005

5.  Assignment of the C5' relative stereochemistry in (+)-lepadin F and (+)-lepadin G and absolute configuration of (+)-lepadin G.

Authors:  Gang Li; Richard P Hsung
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

6.  Lepadins I-K, 3- O-(3'-Methylthio)acryloyloxy-decahydroquinoline Esters from a Bahamian Ascidian Didemnum sp. Assignment of Absolute Stereostructures.

Authors:  Sesselja Ómarsdóttir; Xiao Wang; Hong-Bing Liu; Brendan M Duggan; Tadeusz F Molinski
Journal:  J Org Chem       Date:  2018-10-26       Impact factor: 4.354

Review 7.  Marine antimalarials.

Authors:  Ernesto Fattorusso; Orazio Taglialatela-Scafati
Journal:  Mar Drugs       Date:  2009-04-23       Impact factor: 5.118
  7 in total

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