Literature DB >> 28676718

Toward the total synthesis of luminamicin; an anaerobic antibiotic: construction of highly functionalized cis-decalin containing a bridged ether moiety.

Hiroyasu Ando1, Aoi Kimishima1, Motoyoshi Ohara1, Tomoyasu Hirose1, Takanori Matsumaru1, Hirokazu Takada1, Keisuke Morodome1, Takehiro Miyamoto1, Akihiro Sugawara1, Satoshi Ōmura1, Toshiaki Sunazuka1.   

Abstract

Synthesis of a cis-decalin moiety, containing an oxa-bridged cis-decalin ring system (11-oxatricyclo(5.3.1.1,703,8)undecane), as a key intermediate of the total synthesis of luminamicin (1) was accomplished. One of the essential steps in our synthetic route is construction of a cis-decaline framework using a one-pot Michael addition-aldol reaction. Additionally, the bridged ether moiety was obtained by an intramolecular 1,6-oxa-Michael reaction of a conjugated aldehyde.

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Year:  2017        PMID： 28676718     DOI： 10.1038/ja.2017.77

Source DB:  PubMed          Journal:  J Antibiot (Tokyo)        ISSN： 0021-8820            Impact factor:   2.649


  11 in total

Review 1.  Clostridium difficile infection: update on emerging antibiotic treatment options and antibiotic resistance.

Authors:  Dhara Shah; Minh-Duc Dang; Rodrigo Hasbun; Hoonmo L Koo; Zhi-Dong Jiang; Herbert L DuPont; Kevin W Garey
Journal:  Expert Rev Anti Infect Ther       Date:  2010-05       Impact factor: 5.091

2.  Synthesis of iso-epoxy-amphidinolide N and des-epoxy-caribenolide I structures. Initial forays.

Authors:  K C Nicolaou; William E Brenzovich; Paul G Bulger; Tasha M Francis
Journal:  Org Biomol Chem       Date:  2006-04-26       Impact factor: 3.876

3.  Stereostructure of luminamicin, an anaerobic antibiotic, via molecular dynamics, NMR spectroscopy, and the modified Mosher method.

Authors:  Hiroaki Gouda; Toshiaki Sunazuka; Hideaki Ui; Masaki Handa; Yusuke Sakoh; Yuzuru Iwai; Shuichi Hirono; Satoshi Omura
Journal:  Proc Natl Acad Sci U S A       Date:  2005-12-12       Impact factor: 11.205

Review 4.  Clostridium difficile infection.

Authors:  Daniel A Leffler; J Thomas Lamont
Journal:  N Engl J Med       Date:  2015-04-16       Impact factor: 91.245

5.  Coloradocin, an antibiotic from a new Actinoplanes. I. Taxonomy, fermentation and biological properties.

Authors:  M Jackson; J P Karwowski; R J Theriault; P B Fernandes; R C Semon; W L Kohl
Journal:  J Antibiot (Tokyo)       Date:  1987-10       Impact factor: 2.649

6.  Luminamicin, a new antibiotic. Production, isolation and physico-chemical and biological properties.

Authors:  S Omura; R Iwata; Y Iwai; S Taga; Y Tanaka; H Tomoda
Journal:  J Antibiot (Tokyo)       Date:  1985-10       Impact factor: 2.649

7.  Total synthesis of branimycin: an evolutionary approach.

Authors:  Valentin S Enev; Wolfgang Felzmann; Alexey Gromov; Stefan Marchart; Johann Mulzer
Journal:  Chemistry       Date:  2012-07-04       Impact factor: 5.236

8.  Production, isolation and biological activity of nargenicin from Nocardia sp. CS682.

Authors:  Jae Kyung Sohng; Tokutaro Yamaguchi; Chi Nam Seong; Keun Sik Baik; Seong Chan Park; Hyo Jeong Lee; So Young Jang; Jaya Ram Simkhada; Jin Cheol Yoo
Journal:  Arch Pharm Res       Date:  2008-10-29       Impact factor: 4.946

9.  Coloradocin, an antibiotic from a new Actinoplanes. II. Identity with luminamicin and elucidation of structure.

Authors:  R R Rasmussen; M H Scherr; D N Whittern; A M Buko; J B McAlpine
Journal:  J Antibiot (Tokyo)       Date:  1987-10       Impact factor: 2.649

10.  Reinvestigation of the Branimycin Stereochemistry at Position 17-C.

Authors:  Ana Čikoš; Nicolas Triballeau; Paul A Hubbard; Dinko Žiher; Pieter F W Stouten; Julien G P-O Doyon; Tiny Deschrijver; Johan Wouters; Renaud H M Lépine; Laurent Saniere
Journal:  Org Lett       Date:  2016-02-05       Impact factor: 6.005
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