Literature DB >> 22148850

Total synthesis of (-)-tirandamycin C.

Ming Chen1, William R Roush.   

Abstract

Tirandamycin C is a newly isolated member of the tetramic acid family natural products. We described herein the first enantioselective synthesis of natural (-)-tirandamycin C, the postulated biosynthetic precursor of other members of this family. The highly stereoselective (>15:1) mismatched double asymmetric γ-stannylcrotylboration reaction of aldehyde 8 with crotylborane reagent (R)-E-9 was utilized to access the key anti,anti-stereotriad 18.
© 2011 American Chemical Society

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Year:  2011        PMID： 22148850      PMCID： PMC3253220          DOI： 10.1021/ol203161u

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


  22 in total

1.  Tetramic acid antibiotics: stereoselective synthesis of streptolic acid and tirandalydigin.

Authors:  Yasuhiro Iwata; Naomi Maekawara; Keiji Tanino; Masaaki Miyashita
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-25       Impact factor: 15.336

2.  Structural basis of transcription inhibition by antibiotic streptolydigin.

Authors:  Dmitry Temiakov; Nikolay Zenkin; Marina N Vassylyeva; Anna Perederina; Tahir H Tahirov; Ekaterina Kashkina; Maria Savkina; Savva Zorov; Vadim Nikiforov; Noriyuki Igarashi; Naohiro Matsugaki; Soichi Wakatsuki; Konstantin Severinov; Dmitry G Vassylyev
Journal:  Mol Cell       Date:  2005-09-02       Impact factor: 17.970

Review 3.  Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.

Authors:  Georgios C Vougioukalakis; Robert H Grubbs
Journal:  Chem Rev       Date:  2010-03-10       Impact factor: 60.622

4.  Enantioconvergent hydroboration of a racemic allene: enantioselective synthesis of (E)-δ-stannyl-anti-homoallylic alcohols via aldehyde crotylboration.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

5.  Prevention of undesirable isomerization during olefin metathesis.

Authors:  Soon Hyeok Hong; Daniel P Sanders; Choon Woo Lee; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2005-12-14       Impact factor: 15.419

6.  Characterization of TrdL as a 10-hydroxy dehydrogenase and generation of new analogues from a tirandamycin biosynthetic pathway.

Authors:  Xuhua Mo; Hongbo Huang; Junying Ma; Zhongwen Wang; Bo Wang; Si Zhang; Changsheng Zhang; Jianhua Ju
Journal:  Org Lett       Date:  2011-04-01       Impact factor: 6.005

7.  Tirandamycins from Streptomyces sp. 17944 inhibiting the parasite Brugia malayi asparagine tRNA synthetase.

Authors:  Zhiguo Yu; Sanja Vodanovic-Jankovic; Nathan Ledeboer; Sheng-Xiong Huang; Scott R Rajski; Michael Kron; Ben Shen
Journal:  Org Lett       Date:  2011-03-15       Impact factor: 6.005

8.  Increased efficiency in cross-metathesis reactions of sterically hindered olefins.

Authors:  Ian C Stewart; Christopher J Douglas; Robert H Grubbs
Journal:  Org Lett       Date:  2008-01-05       Impact factor: 6.005

9.  Inhibition of bacterial RNA polymerase by streptolydigin: stabilization of a straight-bridge-helix active-center conformation.

Authors:  Steven Tuske; Stefan G Sarafianos; Xinyue Wang; Brian Hudson; Elena Sineva; Jayanta Mukhopadhyay; Jens J Birktoft; Olivier Leroy; Sajida Ismail; Arthur D Clark; Chhaya Dharia; Andrew Napoli; Oleg Laptenko; Jookyung Lee; Sergei Borukhov; Richard H Ebright; Eddy Arnold
Journal:  Cell       Date:  2005-08-26       Impact factor: 41.582

10.  Tirandamycin biosynthesis is mediated by co-dependent oxidative enzymes.

Authors:  Jacob C Carlson; Shengying Li; Shamila S Gunatilleke; Yojiro Anzai; Douglas A Burr; Larissa M Podust; David H Sherman
Journal:  Nat Chem       Date:  2011-07-17       Impact factor: 24.427
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  13 in total

1.  Enantioselective synthesis of (+)-crocacin C. An example of a highly challenging mismatched double asymmetric δ-stannylcrotylboration reaction.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-03-12       Impact factor: 6.005

Review 2.  Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.

Authors:  K C Nicolaou; Christopher R H Hale; Christian Nilewski; Heraklidia A Ioannidou
Journal:  Chem Soc Rev       Date:  2012-06-28       Impact factor: 54.564

3.  Diastereo- and enantioselective synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via allenylboronate kinetic resolution with ((d)Ipc)2BH and aldehyde allylboration.

Authors:  Jeng-Liang Han; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2012-05-30       Impact factor: 6.005

4.  Enantioselective synthesis of anti- and syn-homopropargyl alcohols via chiral Brønsted acid catalyzed asymmetric allenylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-06-25       Impact factor: 15.419

5.  Crotylboron-based synthesis of the polypropionate units of chaxamycins A/D, salinisporamycin, and rifamycin S.

Authors:  Ming Chen; William R Roush
Journal:  J Org Chem       Date:  2012-06-15       Impact factor: 4.354

6.  Highly stereoselective synthesis of anti,anti-dipropionate stereotriads: a solution to the long-standing problem of challenging mismatched double asymmetric crotylboration reactions.

Authors:  Ming Chen; William R Roush
Journal:  J Am Chem Soc       Date:  2012-02-14       Impact factor: 15.419

7.  Enantioselective synthesis of (E)-δ-silyl-anti-homoallylic alcohols via an enantiodivergent hydroboration-crotylboration reaction of a racemic allenylsilane.

Authors:  Ming Chen; William R Roush
Journal:  Org Lett       Date:  2013-03-27       Impact factor: 6.005

8.  Chiral Brønsted acid catalyzed enantioselective synthesis of anti-homopropargyl alcohols via kinetic resolution-aldehyde allenylboration using racemic allenylboronates.

Authors:  Andy S Tsai; Ming Chen; William R Roush
Journal:  Org Lett       Date:  2013-03-13       Impact factor: 6.005

9.  Enantiodivergent hydroboration reactions of a racemic allenylsilane with diisopinocampheylborane and Curtin-Hammett controlled double asymmetric crotylboration reactions of (S)-E-αphenyldimethylsilyl( d diisopinocampheyl)-crotylborane.

Authors:  Ming Chen; William R Roush
Journal:  Tetrahedron       Date:  2013-09-09       Impact factor: 2.457

10.  Enantiodivergent Hydroboration Reactions of a Racemic Allenylsilane with Diisopinocampheylborane and Curtin-Hammett Controlled Double Asymmetric Crotylboration Reactions of (S)-E-α-phenyldimethylsilyl( d diisopinocampheyl)-crotylborane.

Authors:  Ming Chen; William R Roush
Journal:  Tetrahedron       Date:  2013-07-01       Impact factor: 2.457
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