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Literature DB >> 15277689

Toward the synthesis of the carbacylic ansa antibiotic kendomycin.

Johann Mulzer¹, Stefan Pichlmair, Martin P Green, Maria M B Marques, Harry J Martin.

Abstract

The convergent synthesis of a benzofuran analog of the carbacyclic ansa compound kendomycin has been achieved by assembling three major fragments by means of epoxide opening and directed ortho lithiation. The crucial tetrahydropyran ring was formed by a highly stereoselective cationic cyclization. Analysis of all synthesized tetrahydropyran-arene compounds reveals a hindered sp(2)-sp(3) rotation, which results in rotational isomers or atropisomers affecting macrocyclization reactions. The latter could only be achieved by means of Horner-Wadsworth-Emmons olefination.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2004 PMID： 15277689 PMCID： PMC514420 DOI： 10.1073/pnas.0401503101

Source DB: PubMed Journal: Proc Natl Acad Sci U S A ISSN： 0027-8424 Impact factor: 11.205

6 in total

1. Total synthesis of phorboxazole A.

Authors: David R Williams; Andre A Kiryanov; Ulrich Emde; Michael P Clark; Martin A Berliner; Jonathan T Reeves
Journal: Angew Chem Int Ed Engl Date: 2003-03-17 Impact factor: 15.336

2. Total Synthesis of Lankacyclinol Generous financial support for this research was provided by the National Institutes of Health (Award no.: GM41560). Additionally, a National Institutes of Health Minority Predoctoral Fellowship (Award no.: GM18547) to G.S.C. is gratefully acknowledged. We also wish to thank Dr. Tsuneaki Hida and Dr. Yoshio Kozai, Takeda Chemical Ltd. (Japan), for providing us with an authentic sample of lankacyclinol as well as copies of the original (1)H NMR spectrum.

Authors: David R. Williams; Guillermo S. Cortez; Stéphane L. Bogen; Christian M. Rojas
Journal: Angew Chem Int Ed Engl Date: 2000-12-15 Impact factor: 15.336

3. Synthesis, biological evaluation, and conformational analysis of A-ring diastereomers of 2-methyl-1,25-dihydroxyvitamin D(3) and their 20-epimers: unique activity profiles depending on the stereochemistry of the A-ring and at C-20.

Authors: K Konno; T Fujishima; S Maki; Z Liu; D Miura; M Chokki; S Ishizuka; K Yamaguchi; Y Kan; M Kurihara; N Miyata; C Smith; H F DeLuca; H Takayama
Journal: J Med Chem Date: 2000-11-02 Impact factor: 7.446

4. Total synthesis of Elisabethin A: intramolecular Diels-Alder reaction under biomimetic conditions.

Authors: Thilo J Heckrodt; Johann Mulzer
Journal: J Am Chem Soc Date: 2003-04-23 Impact factor: 15.419

5. A novel approach toward the synthesis of kendomycin: selective synthesis of a C-aryl glycoside as a single atropisomer.

Authors: Stefan Pichlmair; Maria M B Marques; Martin P Green; Harry J Martin; Johann Mulzer
Journal: Org Lett Date: 2003-11-27 Impact factor: 6.005

6. Synthesis of the C1-C13 Fragment of Kendomycin: Atropisomerism around a C-Aryl Glycosidic Bond.

Authors: Harry J Martin; Martina Drescher; Hanspeter Kählig; Sabine Schneider; Johann Mulzer
Journal: Angew Chem Int Ed Engl Date: 2001-09-03 Impact factor: 15.336

6 in total

4 in total

Toward the synthesis of the carbacylic ansa antibiotic kendomycin.

1. Total synthesis of phorboxazole A.

3. Synthesis, biological evaluation, and conformational analysis of A-ring diastereomers of 2-methyl-1,25-dihydroxyvitamin D(3) and their 20-epimers: unique activity profiles depending on the stereochemistry of the A-ring and at C-20.

4. Total synthesis of Elisabethin A: intramolecular Diels-Alder reaction under biomimetic conditions.

5. A novel approach toward the synthesis of kendomycin: selective synthesis of a C-aryl glycoside as a single atropisomer.

6. Synthesis of the C1-C13 Fragment of Kendomycin: Atropisomerism around a C-Aryl Glycosidic Bond.

Review 1. Strategies for construction of the all-carbon macrocyclic skeleton of the ansamycin antibiotic-kendomycin.

Review 2. Prins-type macrocyclizations as an efficient ring-closing strategy in natural product synthesis.

3. Total synthesis of kendomycin: a macro-C-glycosidation approach.

4. Formal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycle.