Literature DB >> 11975617

Total synthesis of (+/-)-stenine using the IMDAF cycloaddition of a 2-methylthio-5-amido-substituted furan.

John D Ginn1, Albert Padwa.   

Abstract

[reaction: see text]. The intramolecular [4 + 2]-cycloaddition of a 2-methylthio-5-amidofuran was used to create the azepinoindole skeleton present in the Stemona alkaloid stenine. The rearranged cycloadduct was converted to stenine (1) in 11 additional steps via a sequence that features a Crabtree catalyst directed hydrogenation (9-->10), iodolactonization (2-->11), and a Keck allylation (11-->12).

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Year:  2002        PMID： 11975617     DOI： 10.1021/ol025746b

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


  13 in total

1.  Studies on a urea-directed Stork-Crabtree hydrogenation. Synthesis of the C1-C9 subunit of (+)-zincophorin.

Authors:  Zhenlei Song; Richard P Hsung; Ting Lu; Andrew G Lohse
Journal:  J Org Chem       Date:  2007-11-03       Impact factor: 4.354

2.  Total synthesis of (+/-)-strychnine via a [4 + 2]-cycloaddition/rearrangement cascade.

Authors:  Hongjun Zhang; Jutatip Boonsombat; Albert Padwa
Journal:  Org Lett       Date:  2007-01-18       Impact factor: 6.005

3.  Application of the aza-Achmatowicz oxidative rearrangement for the stereoselective synthesis of the Cassia and Prosopis alkaloid family.

Authors:  Carolyn A Leverett; Michael P Cassidy; Albert Padwa
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

4.  Synthesis and receptor profiling of Stemona alkaloid analogues reveal a potent class of sigma ligands.

Authors:  Kevin J Frankowski; Vincent Setola; Jon M Evans; Ben Neuenswander; Bryan L Roth; Jeffrey Aubé
Journal:  Proc Natl Acad Sci U S A       Date:  2011-02-28       Impact factor: 11.205

5.  Synthesis of the tetracyclic framework of the erythrina alkaloids using a [4 + 2]-cycloaddition/Rh(I)-catalyzed cascade of 2-imidofurans.

Authors:  Albert Padwa; Qiu Wang
Journal:  J Org Chem       Date:  2006-09-15       Impact factor: 4.354

6.  Rhodium(I)-catalyzed nucleophilic ring-opening reactions of oxabicyclo adducts derived from the [4 + 2]-cycloaddition of 2-imido-substituted furans.

Authors:  Albert Padwa; Qiu Wang
Journal:  J Org Chem       Date:  2006-04-14       Impact factor: 4.354

7.  A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.

Authors:  Gang Li; Lauren J Carlson; Irina K Sagamanova; Brian W Slafer; Richard P Hsung; Claudio Gilardi; Heather M Sklenicka; Nadiya Sydroenko
Journal:  Synthesis (Stuttg)       Date:  2009-09-01       Impact factor: 3.157

8.  A Diastereoselective Intramolecular Pauson-Khand Approach to the Construction of the BC Ring System in Tuberostemoninol.

Authors:  Xiangna Jia; Robert M Williams
Journal:  Tetrahedron Asymmetry       Date:  2008-12-12

9.  A microwave assisted intramolecular-furan-Diels-Alder approach to 4-substituted indoles.

Authors:  Filip Petronijevic; Cody Timmons; Anthony Cuzzupe; Peter Wipf
Journal:  Chem Commun (Camb)       Date:  2008-11-11       Impact factor: 6.222

10.  Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.

Authors:  Qiu Wang; Albert Padwa
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005
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