Literature DB >> 19908916

Progress toward the total synthesis of lucentamycin A: total synthesis and biological evaluation of 8-epi-lucentamycin A.

R Nathan Daniels1, Bruce J Melancon, Emily A Wang, Brenda C Crews, Lawrence J Marnett, Gary A Sulikowski, Craig W Lindsley.   

Abstract

Synthetic efforts toward the cytotoxic peptides lucentamycins A-D are described that resulted in the total synthesis and biological evaluation of 8-epi-lucentamycin A in 15 steps with 2.2% overall yield. The key epi-nonproteogenic 3-methyl-4-ethylideneproline was synthesized via a titanium-mediated cycloisomerization reaction.

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Year:  2009        PMID： 19908916     DOI： 10.1021/jo902115s

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


  7 in total

1.  Covalent Inhibitors of Plasmodium falciparum Glyceraldehyde 3-Phosphate Dehydrogenase with Antimalarial Activity in Vitro.

Authors:  Gregorio Cullia; Stefano Bruno; Silvia Parapini; Marilena Margiotta; Lucia Tamborini; Andrea Pinto; Andrea Galbiati; Andrea Mozzarelli; Marco Persico; Antonella Paladino; Caterina Fattorusso; Donatella Taramelli; Paola Conti
Journal:  ACS Med Chem Lett       Date:  2019-02-20       Impact factor: 4.345

2.  Mechanism-based inactivation by aromatization of the transaminase BioA involved in biotin biosynthesis in Mycobaterium tuberculosis.

Authors:  Ce Shi; Todd W Geders; Sae Woong Park; Daniel J Wilson; Helena I Boshoff; Orishadipe Abayomi; Clifton E Barry; Dirk Schnappinger; Barry C Finzel; Courtney C Aldrich
Journal:  J Am Chem Soc       Date:  2011-10-24       Impact factor: 15.419

3.  Total Synthesis (+)-7-Bromotrypargine and Unnatural Analogs: Biological Evaluation Uncovers Activity at CNS Targets of Therapeutic Relevance.

Authors:  John T Brogan; Sydney L Stoops; Brenda C Crews; Lawrence J Marnett; Craig W Lindsley
Journal:  ACS Chem Neurosci       Date:  2011-11-16       Impact factor: 4.418

4.  Comprehensive Synthesis of Amino Acid-Derived Thiazole Peptidomimetic Analogues to Understand the Enigmatic Drug/Substrate-Binding Site of P-Glycoprotein.

Authors:  Bhargav A Patel; Biebele Abel; Anna Maria Barbuti; Uday Kiran Velagapudi; Zhe-Sheng Chen; Suresh V Ambudkar; Tanaji T Talele
Journal:  J Med Chem       Date:  2018-01-23       Impact factor: 7.446

5.  Total synthesis and structural revision of lucentamycin A.

Authors:  Sujeewa Ranatunga; Chih-Hang Anthony Tang; Chih-Chi Andrew Hu; Juan R Del Valle
Journal:  J Org Chem       Date:  2012-10-16       Impact factor: 4.354

6.  Structure assignment of lucentamycin E and revision of the olefin geometries of the marine-derived lucentamycins.

Authors:  Jin Wook Cha; Jin-Soo Park; Taebo Sim; Sang-Jip Nam; Hak Cheol Kwon; Juan R Del Valle; William Fenical
Journal:  J Nat Prod       Date:  2012-09-06       Impact factor: 4.050

7.  The 2-(triphenylsilyl)ethoxycarbonyl-("Tpseoc"-) group: a new silicon-based, fluoride cleavable oxycarbonyl protecting group highly orthogonal to the Boc-, Fmoc- and Cbz-groups.

Authors:  Martin Golkowski; Thomas Ziegler
Journal:  Molecules       Date:  2011-06-07       Impact factor: 4.411
  7 in total

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