Literature DB >> 24319987

Total synthesis of (-)-calyciphylline N.

Artem Shvartsbart1, Amos B Smith.   

Abstract

The total synthesis of the architecturally complex Daphniphyllum alkaloid (-)-calyciphylline N has been achieved. Highlights of the synthesis include a Et2AlCl-promoted, highly stereoselective, susbtrate-controlled intramolecular Diels-Alder reaction, a transannular enolate alkylation, an effective Stille carbonylation/Nazarov cyclization sequence, and a high-risk diastereoselective hydrogenation of a fully substituted conjugated diene ester.

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Year:  2013        PMID： 24319987      PMCID： PMC3908864          DOI： 10.1021/ja411539w

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


  13 in total

1.  A Practical Synthesis of Difunctional Organosilane Reagents and Their Application to the Diels-Alder Reaction.

Authors:  Scott McN. Sieburth; Jerome Lang
Journal:  J Org Chem       Date:  1999-03-19       Impact factor: 4.354

2.  Expedient construction of the [7-5-5] all-carbon tricyclic core of the Daphniphyllum alkaloids daphnilongeranin B and daphniyunnine D.

Authors:  Benjamin Darses; Iacovos N Michaelides; Filippo Sladojevich; John W Ward; Paula R Rzepa; Darren J Dixon
Journal:  Org Lett       Date:  2012-03-09       Impact factor: 6.005

3.  Total synthesis of (+)-daphmanidin E.

Authors:  Matthias E Weiss; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2011-10-11       Impact factor: 15.336

4.  Daphniyunnines A-E, alkaloids from Daphniphyllum yunnanense.

Authors:  Hua Zhang; Sheng-Ping Yang; Cheng-Qi Fan; Jian Ding; Jian-Min Yue
Journal:  J Nat Prod       Date:  2006-04       Impact factor: 4.050

5.  Daphmanidins E and F, alkaloids from Daphniphyllum teijsmannii.

Authors:  Hiroshi Morita; Nozomi Ishioka; Hiroshi Takatsu; Toru Iizuka; Jun'ichi Kobayashi
Journal:  J Nat Prod       Date:  2006-03       Impact factor: 4.050

6.  Synthesis of the core ring system of the yuzurimine-type Daphniphyllum alkaloids by cascade condensation, cyclization, cycloaddition chemistry.

Authors:  Iain Coldham; Luke Watson; Harry Adams; Nathaniel G Martin
Journal:  J Org Chem       Date:  2011-03-08       Impact factor: 4.354

7.  Unification of anion relay chemistry with the Takeda and Hiyama cross-coupling reactions: identification of an effective silicon-based transfer agent.

Authors:  Amos B Smith; Adam T Hoye; Dionicio Martinez-Solorio; Won-Suk Kim; Rongbiao Tong
Journal:  J Am Chem Soc       Date:  2012-02-29       Impact factor: 15.419

8.  Daphmanidin A, a novel hexacyclic alkaloid from Daphniphyllum teijsmanii.

Authors:  Jun'ichi Kobayashi; Satoshi Ueno; Hiroshi Morita
Journal:  J Org Chem       Date:  2002-09-06       Impact factor: 4.354

9.  Facile cleavage of triethylsilyl (TES) ethers using o-iodoxybenzoic acid (IBX) without affecting tert-butyldimethylsilyl (TBS) ethers.

Authors:  Yikang Wu; Jia-Hui Huang; Xin Shen; Qi Hu; Chao-Jun Tang; Liang Li
Journal:  Org Lett       Date:  2002-06-27       Impact factor: 6.005

Review 10.  The Daphniphyllum alkaloids.

Authors:  Jun'ichi Kobayashi; Takaaki Kubota
Journal:  Nat Prod Rep       Date:  2009-05-08       Impact factor: 13.423
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  5 in total

1.  Calyciphylline B-Type Alkaloids: Total Syntheses of (-)-Daphlongamine H and (-)-Isodaphlongamine H.

Authors:  Cedric L Hugelshofer; Vignesh Palani; Richmond Sarpong
Journal:  J Am Chem Soc       Date:  2019-05-16       Impact factor: 15.419

2.  Toward the ABCD Core of the Calyciphylline A-Type Daphniphyllum Alkaloids: Solvent non-Innocence in Neutral Aminyl Radical Cyclizations.

Authors:  Jennifer L Stockdill; Alberto M Lopez; Ahmad A Ibrahim
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

Review 3.  Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.

Authors:  Martin Büschleb; Stéphane Dorich; Stephen Hanessian; Daniel Tao; Kyle B Schenthal; Larry E Overman
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-02       Impact factor: 15.336

4.  Enantioselective synthesis of (-)-maoecrystal V by enantiodetermining C-H functionalization.

Authors:  Ping Lu; Artur Mailyan; Zhenhua Gu; David M Guptill; Hengbin Wang; Huw M L Davies; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2014-12-11       Impact factor: 15.419

5.  The daphniphyllum alkaloids: total synthesis of (-)-calyciphylline N.

Authors:  Artem Shvartsbart; Amos B Smith
Journal:  J Am Chem Soc       Date:  2015-03-10       Impact factor: 15.419
  5 in total

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