Journal of Antibiotics

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  1. Syntheses of methylated catechins and theaflavins using 2-nitrobenzenesulfonyl group to protect and deactivate phenol.

    Journal of Antibiotics 69(4):299 (2016) PMID 26905756

    An efficient and versatile synthetic method for labile polyphenols was established using 2-nitrobenzenesulfonate (Ns) as a protecting group for phenol. This methodology provides regio- and stereoselective access to a range of methylated catechins, such as methylated epigallocatechin gallates, th...
  2. The first total synthesis and the second- or third-generation approach.

    Journal of Antibiotics 69(4):191 (2016) PMID 27118326

  3. Strategies for construction of the all-carbon macrocyclic skeleton of the ansamycin antibiotic-kendomycin.

    Journal of Antibiotics 69(4):203 (2016) PMID 26860467

    Kendomycin, an ansamycin-type natural product first reported in 1996, possesses a series of attractive bioactivities and a unique all-carbon macrocyclic skeleton. To the date, seven total syntheses, two formal total syntheses and a number of synthetic studies on this hot molecule have been repor...
  4. Proline-based phosphoramidite reagents for the reductive ligation of S-nitrosothiols.

    Journal of Antibiotics 69(4):313 (2016) PMID 26758493 PMCID PMC4848125

    S-Nitrosothiols (RSNOs) have many biological implications but are rarely used in organic synthesis. In this work we report the development of proline-based phosphoramidite substrates that can effectively convert RSNOs to proline-based sulfenamides through a reductive ligation process. A unique p...
  5. The Petasis-Ferrier rearrangement: developments and applications.

    Journal of Antibiotics 69(4):213 (2016) PMID 26732258

    In the mid-1990s, Petasis reexamined a promising but infrequently used rearrangement strategy, the so-called Ferrier-type-II reaction, and provided it with a modern update. Previously, Ferrier had developed a strategy where carbohydrate derivatives would undergo a fragmentation/aldol-type recomb...
  6. Anti-obesity activities of the yoshinone A and the related marine γ-pyrone compounds.

    Journal of Antibiotics 69(4):348 (2016) PMID 26932409

  7. Professor Amos B Smith, III.

    Journal of Antibiotics 69(4):190 (2016) PMID 27118325

  8. The use of fluorescently-tagged apoptolidins in cellular uptake and response studies.

    Journal of Antibiotics 69(4):327 (2016) PMID 26956792

    The apoptolidins are glycomacrolide microbial metabolites reported to be selectively cytotoxic against tumor cells. Using fluorescently tagged active derivatives we demonstrate selective uptake of these four tagged glycomacrolides in cancer cells over healthy human blood cells. We also demonstra...
  9. Total synthesis of ent-(+)-cinanthrenol A.

    Journal of Antibiotics 69(4):280 (2016) PMID 26555362

    The first total synthesis of ent-(+)-cinanthrenol A of potent estrogenic activity was achieved with 10.9% overall yield in 13 steps from commercially available materials. Our synthesis features a photo-promoted oxidative 6π-electron electrocyclization/aromatization for construction of the cyclop...
  10. Natural product-derived quaternary ammonium compounds with potent antimicrobial activity.

    Journal of Antibiotics 69(4):344 (2016) PMID 26577453

  11. Stereoselective access to tubuphenylalanine and tubuvaline: improved Mn-mediated radical additions and assembly of a tubulysin tetrapeptide analog.

    Journal of Antibiotics 69(4):294 (2016) PMID 26883395

    Synthesis of tubuphenylalanine and tubuvaline (Tuv), α-substituted γ-amino acid building blocks for tubulysin family of antimitotic compounds, has been improved using a radical addition reaction in the presence of unprotected hydroxyl functionality. The key carbon-carbon bond construction entail...
  12. Practical synthesis of the C-ring precursor of paclitaxel from 3-methoxytoluene.

    Journal of Antibiotics 69(4):273 (2016) PMID 26860468

    The practical synthesis of the C-ring precursor of paclitaxel starting from 3-methoxytoluene is described. Lipase-catalyzed kinetic resolution of a substituted cyclohexane-1,2-diol, derived from 3-methoxytoluene in three steps, successfully afforded a desired enantiomer with >99% ee, which was t...
  13. Furan-iminium cation cyclization (FIC) in a total synthesis of manzamine alkaloids.

    Journal of Antibiotics 69(4):340 (2016) PMID 26956791

  14. Amos B Smith, III: chemist, collaborator and mentor.

    Journal of Antibiotics 69(4):189 (2016) PMID 27118324

  15. Synthesis and structure-activity relationship study of FD-891: importance of the side chain and C8-C9 epoxide for cytotoxic activity against cancer cells.

    Journal of Antibiotics 69(4):287 (2016) PMID 26814671

    Unified synthesis of FD-891 analogs and their structure-activity relationship are described. By using stereoselective allylation/crotylation and Evans aldol chemistry, six side-chain fragments having different length and terminus were synthesized. These fragments were coupled with a macrolactone...
  16. Synthesis of the phorboxazoles-potent, architecturally novel marine natural products.

    Journal of Antibiotics 69(4):220 (2016) PMID 26956795

    The phorboxazoles have attracted the attention of synthetic chemists around the globe due to their potent biological activity and novel structure. A review of the recent synthetic efforts as well as new phorboxazole analogs is discussed.
  17. Synthetic studies toward citrinadin A: construction of the pentacyclic core.

    Journal of Antibiotics 69(4):331 (2016) PMID 26956798

    This manuscript describes the preparation of an advanced intermediate toward the total synthesis of citrinadin A, featuring a [3+2] cycloaddition employing in situ generation of the dipole.
  18. The enantioselective synthesis and biological evaluation of chimeric promysalin analogs facilitated by diverted total synthesis.

    Journal of Antibiotics 69(4):337 (2016) PMID 26860469

  19. Non-antibiotic 12-membered macrolides: design, synthesis and biological evaluation in a cigarette-smoking model.

    Journal of Antibiotics 69(4):319 (2016) PMID 26419414

    The 14-membered macrolide erythromycin A expresses three distinct biological properties, including antibacterial activity, gastrointestinal motor-stimulating activity and anti-inflammatory and/or immunomodulatory effects. Although low-dose, long-term therapy using 14- and 15-membered macrolides ...
  20. Organic synthesis in the Smith Group: a personal selection of a dozen lessons learned at the University of Pennsylvania.

    Journal of Antibiotics 69(4):192 (2016) PMID 26932408

    The passionate study of the complex and ever-evolving discipline of organic synthesis over more than a four-decade span is certain to elucidate meaningful and significant lessons. Over this period, Amos B. Smith III, the Rhodes-Thompson Professor of Chemistry and Member of the Monell Chemical Se...