Literature DB >> 23067058

Complex polycyclic scaffolds by metathesis rearrangement of Himbert arene/allene cycloadducts.

Jonathan K Lam1, Yvonne Schmidt, Christopher D Vanderwal.   

Abstract

The intramolecular arene/allene cycloaddition first described 30 years ago by Himbert and Henn permits rapid access to strained polycyclic compounds. Alkene metathesis processes cleanly rearrange appropriately substituted cycloadducts into complex, functional-group-rich polycyclic lactams of potential utility for natural product synthesis and medicinal chemistry.

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Year:  2012        PMID： 23067058     DOI： 10.1021/ol302680m

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


  7 in total

1.  Computation and experiment reveal that the ring-rearrangement metathesis of Himbert cycloadducts can be subject to kinetic or thermodynamic control.

Authors:  Jonathan K Lam; Hung V Pham; K N Houk; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2013-11-06       Impact factor: 15.419

Review 2.  Acyclic Twisted Amides.

Authors:  Guangrong Meng; Jin Zhang; Michal Szostak
Journal:  Chem Rev       Date:  2021-08-18       Impact factor: 72.087

3.  Studies on the Himbert intramolecular arene/allene Diels-Alder cycloaddition. Mechanistic studies and expansion of scope to all-carbon tethers.

Authors:  Yvonne Schmidt; Jonathan K Lam; Hung V Pham; K N Houk; Christopher D Vanderwal
Journal:  J Am Chem Soc       Date:  2013-05-01       Impact factor: 15.419

Review 4.  Recent advances in the development of polycyclic skeletons via Ugi reaction cascades.

Authors:  Jie Lei; Jiang-Ping Meng; Dian-Yong Tang; Brendan Frett; Zhong-Zhu Chen; Zhi-Gang Xu
Journal:  Mol Divers       Date:  2018-01-16       Impact factor: 2.943

5.  Diels-Alder reactions of allene with benzene and butadiene: concerted, stepwise, and ambimodal transition states.

Authors:  Hung V Pham; K N Houk
Journal:  J Org Chem       Date:  2014-09-18       Impact factor: 4.354

Review 6.  Recent applications of ring-rearrangement metathesis in organic synthesis.

Authors:  Sambasivarao Kotha; Milind Meshram; Priti Khedkar; Shaibal Banerjee; Deepak Deodhar
Journal:  Beilstein J Org Chem       Date:  2015-10-07       Impact factor: 2.883

7.  Application of New Efficient Hoveyda-Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles.

Authors:  Alexandra S Antonova; Marina A Vinokurova; Pavel A Kumandin; Natalia L Merkulova; Anna A Sinelshchikova; Mikhail S Grigoriev; Roman A Novikov; Vladimir V Kouznetsov; Kirill B Polyanskii; Fedor I Zubkov
Journal:  Molecules       Date:  2020-11-17       Impact factor: 4.411
  7 in total

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