Literature DB >> 21591684

Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates.

Stephen N Greszler1, Justin T Malinowski, Jeffrey S Johnson.   

Abstract

A formal synthesis of leustroducsin B has been completed. The synthesis relies upon a recently developed Reformatsky/Claisen condensation of silyl glyoxylates and enantioenriched β-lactones that establishes two of the molecule's three core stereocenters and permits further elaboration to an intermediate in Imanishi's synthesis via reliable chemistry (Prasad reduction, asymmetric pentenylation, Mitsunobu inversion).
© 2011 American Chemical Society

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Year:  2011        PMID： 21591684      PMCID： PMC3115596          DOI： 10.1021/ol2011192

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


  28 in total

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5.  Studies on new phosphate ester antifungal antibiotics phoslactomycins. II. Structure elucidation of phoslactomycins A to F.

Authors:  S Fushimi; K Furihata; H Seto
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Journal:  J Antibiot (Tokyo)       Date:  2007-12       Impact factor: 2.649

7.  Asymmetric total synthesis of (+)-phoslactomycin B.

Authors:  Setsuya Shibahara; Masataka Fujino; Yasumasa Tashiro; Keisuke Takahashi; Jun Ishihara; Susumi Hatakeyama
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8.  Catalytic asymmetric acyl halide-aldehyde cyclocondensation reactions of substituted ketenes.

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Review 9.  Fostriecin: chemistry and biology.

Authors:  D S Lewy; C-M Gauss; D R Soenen; D L Boger
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Authors:  T Kohama; H Maeda; J I Sakai; A Shiraishi; K Yamashita
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5.  Silyl glyoxylates. Conception and realization of flexible conjunctive reagents for multicomponent coupling.

Authors:  Gregory R Boyce; Stephen N Greszler; Jeffrey S Johnson; Xin Linghu; Justin T Malinowski; David A Nicewicz; Andrew D Satterfield; Daniel C Schmitt; Kimberly M Steward
Journal:  J Org Chem       Date:  2012-03-23       Impact factor: 4.354

6.  A Highly Convergent Total Synthesis of Leustroducsin B.

Authors:  Barry M Trost; Berenger Biannic; Cheyenne S Brindle; B Michael O'Keefe; Thomas J Hunter; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2015-09-01       Impact factor: 15.419

7.  Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition.

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8.  Alternaric acid: formal synthesis and related studies.

Authors:  Michael C Slade; Jeffrey S Johnson
Journal:  Beilstein J Org Chem       Date:  2013-01-24       Impact factor: 2.883
  8 in total

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