Literature DB >> 18722441

Total synthesis of haterumalides NA and NC via a chromium-mediated macrocyclization.

Jennifer M Schomaker1, Babak Borhan.   

Abstract

The syntheses of haterumalides NA and NC were accomplished via the macrocyclization of a chlorovinylidene chromium carbenoid onto a pendant aldehyde to generate the C8-C9 bond with the desired stereoisomer as the major product. Utilizing the latter chemistry enables access to both C9 hydroxylated (haterumalides NC and ND) and C9 deoxygenated forms (haterumalides NA, NB, and NE; via deoxygenation of the C9-hydroxyl).

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Year:  2008        PMID： 18722441      PMCID： PMC2659614          DOI： 10.1021/ja8043695

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


  8 in total

1.  Stereoselective C-glycosylation reactions of ribose derivatives: electronic effects of five-membered ring oxocarbenium ions.

Authors:  Catharine H Larsen; Brian H Ridgway; Jared T Shaw; Deborah M Smith; K A Woerpel
Journal:  J Am Chem Soc       Date:  2005-08-10       Impact factor: 15.419

2.  Second-generation total synthesis of haterumalide NA using B-alkyl Suzuki-Miyaura coupling.

Authors:  Ichiro Hayakawa; Mitsuru Ueda; Masashi Yamaura; Yoichi Ikeda; Yuta Suzuki; Kensaku Yoshizato; Hideo Kigoshi
Journal:  Org Lett       Date:  2008-04-09       Impact factor: 6.005

3.  Chromium vinylidene carbenoids: generation, characterization, and reactivity. First evidence for an internal proton return phenomenon with vinylidene carbenoids.

Authors:  R Baati; D K Barma; J R Falck; C Mioskowski
Journal:  J Am Chem Soc       Date:  2001-09-19       Impact factor: 15.419

4.  Alkyne haloallylation [with Pd(II)] as a core strategy for macrocycle synthesis: a total synthesis of (-)-haterumalide NA/(-)-oocydin A.

Authors:  Thomas R Hoye; Jizhou Wang
Journal:  J Am Chem Soc       Date:  2005-05-18       Impact factor: 15.419

Review 5.  Marine cytotoxic macrolides haterumalides and biselides, and related natural products.

Authors:  Hideo Kigoshi; Ichiro Hayakawa
Journal:  Chem Rec       Date:  2007       Impact factor: 6.771

6.  Synthesis of ent-haterumalide NA (ent-oocydin A) methyl ester.

Authors:  Yonghong Gu; Barry B Snider
Journal:  Org Lett       Date:  2003-11-13       Impact factor: 6.005

7.  Enantioselective synthesis of 15-epi-haterumalide NA methyl ester and revised structure of haterumalide NA.

Authors:  Hideo Kigoshi; Masaki Kita; Seiji Ogawa; Masahiro Itoh; Daisuke Uemura
Journal:  Org Lett       Date:  2003-03-20       Impact factor: 6.005

8.  Total synthesis of (+)-oocydin A: application of the Suzuki-Miyaura cross-coupling of 1,1-dichloro-1-alkenes with 9-alkyl 9-BBN.

Authors:  Emmanuel Roulland
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336
  8 in total
  3 in total

1.  Diastereoselective, three-component cascade synthesis of tetrahydrofurans and tetrahydropyrans employing the tandem Mukaiyama aldol-lactonization process.

Authors:  T Andrew Mitchell; Cunxiang Zhao; Daniel Romo
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

2.  Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Authors:  Matthew S McCammant; Longyan Liao; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2013-03-12       Impact factor: 15.419

3.  Chagosensine: A Riddle Wrapped in a Mystery Inside an Enigma.

Authors:  Marc Heinrich; John J Murphy; Marina K Ilg; Aurélien Letort; Jakub T Flasz; Petra Philipps; Alois Fürstner
Journal:  J Am Chem Soc       Date:  2020-03-20       Impact factor: 15.419
  3 in total

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