Literature DB >> 17997560

Total synthesis of (-)-okilactomycin.

Amos B Smith1, Kallol Basu, Todd Bosanac.   

Abstract

A highly convergent synthesis of (-)-okilactomycin is described. Key reactions of this synthesis include a strategy-level diastereoselective oxy-Cope rearrangement/oxidation sequence, a Petasis-Ferrier union/rearrangement tactic, and an efficient RCM reaction to construct the 13-membered macrocyclic ring.

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Year:  2007        PMID： 17997560     DOI： 10.1021/ja077569l

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  20 in total

1.  Spongipyran Synthetic Studies. Evolution of a Scalable Total Synthesis of (+)-Spongistatin 1.

Authors:  Amos B Smith; Chris Sfouggatakis; Christina A Risatti; Jeffrey B Sperry; Wenyu Zhu; Victoria A Doughty; Takashi Tomioka; Dimitar B Gotchev; Clay S Bennett; Satoshi Sakamoto; Onur Atasoylu; Shohei Shirakami; David Bauer; Makoto Takeuchi; Jyunichi Koyanagi; Yasuharu Sakamoto
Journal:  Tetrahedron       Date:  2009-09-15       Impact factor: 2.457

2.  Mechanistic Analysis of Oxidative C-H Cleavages Using Inter- and Intramolecular Kinetic Isotope Effects.

Authors:  Hyung Hoon Jung; Paul E Floreancig
Journal:  Tetrahedron       Date:  2009-12-26       Impact factor: 2.457

3.  A concise total synthesis of (±)- and (-)-okilactomycin D.

Authors:  Dawen Niu; Thomas R Hoye
Journal:  Org Lett       Date:  2012-01-24       Impact factor: 6.005

4.  Phorboxazole Synthetic Studies: Design, Synthesis and Biological Evaluation of Phorboxazole A and Hemi-Phorboxazole A Related Analogues.

Authors:  Amos B Smith; Anne-Marie L Hogan; Zhuqing Liu; Thomas M Razler; Regina M Meis; Brandon I Morinaka; Tadeusz F Molinski
Journal:  Tetrahedron       Date:  2011-07-08       Impact factor: 2.457

5.  Synthesis of (-)-okilactomycin by a Prins-type fragment-assembly strategy.

Authors:  Jason M Tenenbaum; William J Morris; Daniel W Custar; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-10       Impact factor: 15.336

6.  Organic synthesis in the Smith Group: a personal selection of a dozen lessons learned at the University of Pennsylvania.

Authors:  Kevin P C Minbiole
Journal:  J Antibiot (Tokyo)       Date:  2016-03-02       Impact factor: 2.649

7.  Targeted Covalent Inhibition of Telomerase.

Authors:  Rick C Betori; Yue Liu; Rama K Mishra; Scott B Cohen; Stephen J Kron; Karl A Scheidt
Journal:  ACS Chem Biol       Date:  2020-02-24       Impact factor: 5.100

8.  Pyranone natural products as inspirations for catalytic reaction discovery and development.

Authors:  Benjamin R McDonald; Karl A Scheidt
Journal:  Acc Chem Res       Date:  2015-03-06       Impact factor: 22.384

9.  Evolution of the total synthesis of (-)-okilactomycin exploiting a tandem oxy-cope rearrangement/oxidation, a Petasis-Ferrier union/rearrangement, and ring-closing metathesis.

Authors:  Amos B Smith; Todd Bosanac; Kallol Basu
Journal:  J Am Chem Soc       Date:  2009-02-18       Impact factor: 15.419

Review 10.  The Petasis-Ferrier rearrangement: developments and applications.

Authors:  Emily C Minbiole; Kevin P C Minbiole
Journal:  J Antibiot (Tokyo)       Date:  2016-01-06       Impact factor: 2.649
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