Literature DB >> 12236749

Development of the [3 + 2] annulations of cyclohexenylsilanes and chlorosulfonyl isocyanate: application to the total synthesis of (+/-)-peduncularine.

Claudia W Roberson1, K A Woerpel.   

Abstract

The synthesis of (+/-)-peduncularine was accomplished using the [3 + 2] annulation of an allylic silane with chlorosulfonyl isocyanate to assemble the bicyclic core of the alkaloid. The stereochemistry of the annulation product was employed to control the installation of the indolylmethyl side chain at C-7 with complete stereoselectivity.

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Year:  2002        PMID： 12236749     DOI： 10.1021/ja012152f

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


  9 in total

1.  Au-catalyzed synthesis of 2-alkylindoles from N-arylhydroxylamines and terminal alkynes.

Authors:  Yanzhao Wang; Longwu Ye; Liming Zhang
Journal:  Chem Commun (Camb)       Date:  2011-06-03       Impact factor: 6.222

2.  Remote control of diastereoselectivity in intramolecular reactions of chiral allylsilanes.

Authors:  Weston R Judd; Sooho Ban; Jeffrey Aubé
Journal:  J Am Chem Soc       Date:  2006-10-25       Impact factor: 15.419

3.  Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

Authors:  Zhiguo Bian; Christopher C Marvin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

4.  Regioselective allene hydrosilylation catalyzed by N-heterocyclic carbene complexes of nickel and palladium.

Authors:  Zachary D Miller; Wei Li; Tomás R Belderrain; John Montgomery
Journal:  J Am Chem Soc       Date:  2013-10-03       Impact factor: 15.419

5.  Total synthesis of amphidinolide E.

Authors:  Porino Va; William R Roush
Journal:  J Am Chem Soc       Date:  2006-12-20       Impact factor: 15.419

6.  Total Synthesis of Amphidinolide E and Amphidinolide E Stereoisomers.

Authors:  Porino Va; William R Roush
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

7.  Combining Zn Ion Catalysis with Homogeneous Gold Catalysis: An Efficient Annulation Approach to N-Protected Indoles.

Authors:  Yanzhao Wang; Lianzhu Liu; Liming Zhang
Journal:  Chem Sci       Date:  2013-02-01       Impact factor: 9.825

8.  Carbamoyl radical-mediated synthesis and semipinacol rearrangement of β-lactam diols.

Authors:  Marie Betou; Louise Male; Jonathan W Steed; Richard S Grainger
Journal:  Chemistry       Date:  2014-04-07       Impact factor: 5.236

9.  Enantioselective total syntheses of citrinadins A and B. Stereochemical revision of their assigned structures.

Authors:  Zhiguo Bian; Christopher C Marvin; Martin Pettersson; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2014-09-29       Impact factor: 15.419
  9 in total

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