Literature DB >> 19812680

The first transannular [4+3] cycloaddition reaction: synthesis of the ABCD ring structure of cortistatins.

Derek T Craft1, Benjamin W Gung.   

Abstract

A 14-membered macrocycle with an allene and a furan strategically located at across the ring from each other is synthesized using an allene ring closing metathesis reaction. Upon treatment of the macrocycle with a catalytic amount of Pd(OAc)(2) and other additives, the first transannular [4+3] cycloaddition occurred to yield 37% of a tetracyclic compound containing the ABC ring structure of the natural products cortistatins.

Entities:  

Year:  2008        PMID： 19812680      PMCID： PMC2597840          DOI： 10.1016/j.tetlet.2008.07.155

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  17 in total

1.  Total synthesis of (-)-spinosyn A.

Authors:  Dustin J Mergott; Scott A Frank; William R Roush
Journal:  Proc Natl Acad Sci U S A       Date:  2004-06-01       Impact factor: 11.205

2.  8-Oxabicyclo[3.2.1]oct-6-en-3-ones: application to the asymmetric synthesis of polyoxygenated building blocks.

Authors:  Ingo V Hartung; H Martin R Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2004-04-02       Impact factor: 15.336

3.  Olefin-metathesis catalysts for the preparation of molecules and materials (Nobel Lecture).

Authors:  Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-02       Impact factor: 15.336

4.  Platinum-catalyzed intramolecular [4C+3C] cycloaddition between dienes and allenes.

Authors:  Beatriz Trillo; Fernando López; Moisés Gulías; Luis Castedo; José L Mascareñas
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 5.  Exploration of fundamental and synthetic aspects of the intramolecular 4 + 3 cycloaddition reaction.

Authors:  M Harmata
Journal:  Acc Chem Res       Date:  2001-07       Impact factor: 22.384

6.  Chiral Lewis acid-catalyzed highly enantioselective [4 + 3] cycloaddition reactions of nitrogen-stabilized oxyallyl cations derived from allenamides.

Authors:  Jian Huang; Richard P Hsung
Journal:  J Am Chem Soc       Date:  2005-01-12       Impact factor: 15.419

Review 7.  Electrophilic activation of alkenes by platinum(II): so much more than a slow version of palladium(II).

Authors:  Anthony R Chianese; Stephen J Lee; Michel R Gagné
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  PtCl2-catalyzed rapid access to tetracyclic 2,3-indoline-fused cyclopentenes: reactivity divergent from cationic Au(I) catalysis and synthetic potential.

Authors:  Guozhu Zhang; Vincent J Catalano; Liming Zhang
Journal:  J Am Chem Soc       Date:  2007-08-28       Impact factor: 15.419

9.  A tandem epoxidation/stereoselective intramolecular [4+3] cycloaddition reaction involving nitrogen-stabilized oxyallyl cations derived from chiral allenamides.

Authors:  Challeppan Rameshkumar; Richard P Hsung
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-01       Impact factor: 15.336

10.  Synthesis of (+)-cortistatin A.

Authors:  Ryan A Shenvi; Carlos A Guerrero; Jun Shi; Chuang-Chuang Li; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-05-14       Impact factor: 15.419
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  16 in total

Review 1.  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

2.  Formal total synthesis of (±)-cortistatin A.

Authors:  Eric M Simmons; Alison R Hardin-Narayan; Xuelei Guo; Richmond Sarpong
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

3.  Synthetic studies toward (+)-cortistatin A.

Authors:  Zhang Wang; Mingji Dai; Peter K Park; Samuel J Danishefsky
Journal:  Tetrahedron       Date:  2011-10-29       Impact factor: 2.457

4.  Developing a diastereoselective intramolecular [4+3] cycloaddition of nitrogen-stabilized oxyallyl cations derived from N-sulfonyl-substituted allenamides.

Authors:  Andrew G Lohse; Richard P Hsung; Mitchell D Leider; Sunil K Ghosh
Journal:  J Org Chem       Date:  2011-04-08       Impact factor: 4.354

5.  The Chemistry and Biology of Nakiterpiosin - C-nor-D-Homosteroids.

Authors:  Shuanhu Gao; Qiaoling Wang; Gelin Wang; Brett Lomenick; Jie Liu; Chih-Wei Fan; Lih-Wen Deng; Jing Huang; Lawrence Lum; Chuo Chen
Journal:  Synlett       Date:  2012-10       Impact factor: 2.454

6.  Synthesis of the Cortistatin Pentacyclic Core by Alkoxide-Directed Metallacycle-Mediated Annulative Cross-Coupling.

Authors:  Claudio Aquino; Stephen N Greszler; Glenn C Micalizio
Journal:  Org Lett       Date:  2016-05-19       Impact factor: 6.005

7.  Chemoselectivity: the mother of invention in total synthesis.

Authors:  Ryan A Shenvi; Daniel P O'Malley; Phil S Baran
Journal:  Acc Chem Res       Date:  2009-04-21       Impact factor: 22.384

8.  Synthesis of cortistatins A, J, K and L.

Authors:  Alec N Flyer; Chong Si; Andrew G Myers
Journal:  Nat Chem       Date:  2010-08-01       Impact factor: 24.427

9.  Gold-catalyzed transannular [4+3] cycloaddition reactions.

Authors:  Benjamin W Gung; Derek T Craft; Lauren N Bailey; Kristin Kirschbaum
Journal:  Chemistry       Date:  2010-01-11       Impact factor: 5.236

10.  A hypervalent iodine-induced double annulation enables a concise synthesis of the pentacyclic core structure of the cortistatins.

Authors:  Jessica L Frie; Christopher S Jeffrey; Erik J Sorensen
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005
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