Literature DB >> 19213001

A total synthesis of norhalichondrin B.

Katrina L Jackson1, James A Henderson, Hajime Motoyoshi, Andrew J Phillips.   

Abstract

Four corners: The syntheses of four key building blocks for the total synthesis of norhalichondrin B (see structure) are described. The assembly of these subunits into the natural product is also reported. Key features of the synthesis are the use of the Achmatowicz oxidation/ionic hydrogenation for the synthesis of pyrans and pyranopyrans, and the application of tandem metathesis for the synthesis of pyranopyrans.

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Year:  2009        PMID： 19213001      PMCID： PMC2901598          DOI： 10.1002/anie.200806111

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  18 in total

1.  Acid-Catalyzed Reactions of Homohalichondrin B, a Marine Sponge-Derived Antitumor Polyether Macrolide.

Authors:  Joanne B. Hart; John W. Blunt; Murray H. G. Munro
Journal:  J Org Chem       Date:  1996-04-19       Impact factor: 4.354

2.  Asymmetric Ni(II)/Cr(II)-mediated coupling reaction: catalytic process.

Authors:  Hyeong-Wook Choi; Katsumasa Nakajima; Damtew Demeke; Fu-An Kang; Hyuk-Sang Jun; Zhao-Kui Wan; Yoshito Kishi
Journal:  Org Lett       Date:  2002-12-12       Impact factor: 6.005

3.  A simple but remarkably effective device for forming the C8-C14 polycyclic ring system of halichondrin B.

Authors:  Kosuke Namba; Hyuk-Sang Jun; Yoshito Kishi
Journal:  J Am Chem Soc       Date:  2004-06-30       Impact factor: 15.419

4.  Intramolecular generation and [2,3]-sigmatropic rearrangement of oxonium ylides.

Authors:  M C Pirrung; J A Werner
Journal:  J Am Chem Soc       Date:  1986-09-01       Impact factor: 15.419

5.  New catalytic cycle for couplings of aldehydes with organochromium reagents.

Authors:  Kosuke Namba; Yoshito Kishi
Journal:  Org Lett       Date:  2004-12-23       Impact factor: 6.005

6.  Total synthesis of aburatubolactam A.

Authors:  James A Henderson; Andrew J Phillips
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

7.  Total synthesis of (+)-cyanthiwigin U.

Authors:  Matthew W B Pfeiffer; Andrew J Phillips
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

8.  Operationally simple and efficient workup procedure for TBAF-mediated desilylation: application to halichondrin synthesis.

Authors:  Yosuke Kaburagi; Yoshito Kishi
Journal:  Org Lett       Date:  2007-02-15       Impact factor: 6.005

9.  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

10.  Origin of stereoselectivity in the reduction of a planar oxacarbenium.

Authors:  Joann M Um; K N Houk; Andrew J Phillips
Journal:  Org Lett       Date:  2008-07-23       Impact factor: 6.005
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  14 in total

1.  Reversal of the regiochemistry in the rhodium-catalyzed [4+3] cycloaddition between vinyldiazoacetates and dienes.

Authors:  Pablo E Guzmán; Yajing Lian; Huw M L Davies
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-29       Impact factor: 15.336

2.  Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.

Authors:  Arun K Ghosh; Margherita Brindisi
Journal:  RSC Adv       Date:  2016-11-24       Impact factor: 3.361

Review 3.  Recent advances in ruthenium-based olefin metathesis.

Authors:  O M Ogba; N C Warner; D J O'Leary; R H Grubbs
Journal:  Chem Soc Rev       Date:  2018-06-18       Impact factor: 54.564

4.  Synthesis of the WXYZA' domain of maitotoxin.

Authors:  K C Nicolaou; Thomas M Baker; Tsuyoshi Nakamura
Journal:  J Am Chem Soc       Date:  2010-12-17       Impact factor: 15.419

5.  Synthesis of the C'D'E'F' domain of maitotoxin.

Authors:  K C Nicolaou; Jae Hong Seo; Tsuyoshi Nakamura; Robert J Aversa
Journal:  J Am Chem Soc       Date:  2010-12-17       Impact factor: 15.419

6.  Formal synthesis of (-)-englerin A and cytotoxicity studies of truncated englerins.

Authors:  Jing Xu; Eduardo J E Caro-Diaz; Ayse Batova; Steven D E Sullivan; Emmanuel A Theodorakis
Journal:  Chem Asian J       Date:  2012-03-13

7.  Synthesis of the ABCDEFG ring system of maitotoxin.

Authors:  K C Nicolaou; Robert J Aversa; Jian Jin; Fatima Rivas
Journal:  J Am Chem Soc       Date:  2010-05-19       Impact factor: 15.419

8.  Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction.

Authors:  Jing Xu; Eduardo J E Caro-Diaz; Emmanuel A Theodorakis
Journal:  Org Lett       Date:  2010-08-20       Impact factor: 6.005

9.  Second generation synthesis of C27-C35 building block of E7389, a synthetic halichondrin analogue.

Authors:  Yu-Rong Yang; Dae-Shik Kim; Yoshito Kishi
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

10.  Synthesis of the C(18)-C(34) fragment of amphidinolide C and the C(18)-C(29) fragment of amphidinolide F.

Authors:  Sudeshna Roy; Christopher D Spilling
Journal:  Org Lett       Date:  2010-10-28       Impact factor: 6.005
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