An Expeditious Route to Both Enantiomers of All Carbon Quaternary Stereocenters at C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement: Total Synthesis of (−)-Physostigmine

Ganesh Pandey; Jagadish Khamrai; Akash Mishra

doi:10.1021/ol503766y

An Expeditious Route to Both Enantiomers of All Carbon Quaternary Stereocenters at C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement: Total Synthesis of (−)-Physostigmine

Organic Letters ◽

10.1021/ol503766y ◽

2015 ◽

Vol 17 (4) ◽

pp. 952-955 ◽

Cited By ~ 15

Author(s):

Ganesh Pandey ◽

Jagadish Khamrai ◽

Akash Mishra

Keyword(s):

Total Synthesis ◽

Sigmatropic Rearrangement ◽

Quaternary Stereocenters

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Retraction of “An Expeditious Route to Both Enantiomers of All Carbon Quaternary Stereocenters at C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement: Total Synthesis of (−)-Physostigmine”

Organic Letters ◽

10.1021/acs.orglett.7b03188 ◽

2017 ◽

Vol 19 (22) ◽

pp. 6264-6264 ◽

Cited By ~ 1

Author(s):

Ganesh Pandey ◽

Jagadish Khamrai ◽

Akash Mishra

Keyword(s):

Total Synthesis ◽

Sigmatropic Rearrangement ◽

Quaternary Stereocenters

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Synthesis of Cyclopentenones with C4-Quaternary Stereocenters via Stereospecific [3,3]-Sigmatropic Rearrangement and Applications in Total Synthesis of Sesquiterpenoids

Journal of the American Chemical Society ◽

10.1021/jacs.1c07966 ◽

2021 ◽

Author(s):

Weiping Zhou ◽

Arnaud Voituriez

Keyword(s):

Total Synthesis ◽

Sigmatropic Rearrangement ◽

Quaternary Stereocenters

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Generation of All-Carbon Quaternary Stereocenters at the C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement and Revision of Absolute Configuration: Total Synthesis of (−)-Physostigmine

Organic Letters ◽

10.1021/acs.orglett.7b03537 ◽

2017 ◽

Vol 20 (1) ◽

pp. 166-169 ◽

Cited By ~ 9

Author(s):

Ganesh Pandey ◽

Jagadish Khamrai ◽

Akash Mishra

Keyword(s):

Total Synthesis ◽

Absolute Configuration ◽

Sigmatropic Rearrangement ◽

Quaternary Stereocenters

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ChemInform Abstract: An Expeditious Route to Both Enantiomers of All Carbon Quaternary Stereocenters at C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement: Total Synthesis of (-)-Physostigmine.

ChemInform ◽

10.1002/chin.201528258 ◽

2015 ◽

Vol 46 (28) ◽

pp. no-no

Author(s):

Ganesh Pandey ◽

Jagadish Khamrai ◽

Akash Mishra

Keyword(s):

Total Synthesis ◽

Sigmatropic Rearrangement ◽

Quaternary Stereocenters

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ChemInform Abstract: Domino Double Michael-Claisen Cyclizations: A Powerful General Tool for Introducing Quaternary Stereocenters at C(4) of Cyclohexane-1,3-diones and Total Synthesis of Diverse Families of Sterically Congested Alkaloids.

ChemInform ◽

10.1002/chin.200907061 ◽

2009 ◽

Vol 40 (7) ◽

Author(s):

Teruhiko Ishikawa ◽

Kazuhiro Kudo ◽

Ken Kuroyabu ◽

Satoshi Uchida ◽

Takayuki Kudoh ◽

...

Keyword(s):

Total Synthesis ◽

Diverse Families ◽

Quaternary Stereocenters ◽

General Tool

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Total synthesis of a protected form of sphingofungin E using the [3,3]-sigmatropic rearrangement of an allylic thiocyanate as the key reaction

Carbohydrate Research ◽

10.1016/j.carres.2010.09.016 ◽

2010 ◽

Vol 345 (17) ◽

pp. 2427-2437 ◽

Cited By ~ 17

Author(s):

Miroslava Martinková ◽

Jozef Gonda ◽

Jana Špaková Raschmanová ◽

Michaela Slaninková ◽

Juraj Kuchár

Keyword(s):

Total Synthesis ◽

Sigmatropic Rearrangement

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Total Synthesis of (±)-Kainic Acid with an Aza-[2,3]-Wittig Sigmatropic Rearrangement as the Key Stereochemical Determining Step

The Journal of Organic Chemistry ◽

10.1021/jo030101q ◽

2003 ◽

Vol 68 (16) ◽

pp. 6160-6163 ◽

Cited By ~ 21

Author(s):

James C. Anderson ◽

Matthew Whiting

Keyword(s):

Total Synthesis ◽

Kainic Acid ◽

Sigmatropic Rearrangement

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Total Synthesis of (−)-Agelastatin A: The Application of a Sequential Sigmatropic Rearrangement

Organic Letters ◽

10.1021/ol900799e ◽

2009 ◽

Vol 11 (12) ◽

pp. 2687-2690 ◽

Cited By ~ 66

Author(s):

Naoto Hama ◽

Tomoki Matsuda ◽

Takaaki Sato ◽

Noritaka Chida

Keyword(s):

Total Synthesis ◽

Sigmatropic Rearrangement ◽

Agelastatin A

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Total Synthesis of Mesembrine - The Construction of Quaternary Stereocenters by Gold-Catalyzed Diyne Desymmetrization

Israel Journal of Chemistry ◽

10.1002/ijch.201700060 ◽

2018 ◽

Vol 58 (5) ◽

pp. 568-577 ◽

Cited By ~ 4

Author(s):

Constantin Czekelius

Keyword(s):

Total Synthesis ◽

Quaternary Stereocenters

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Identification of an unexpected 2-oxonia[3,3]sigmatropic rearrangement/aldol pathway in the formation of oxacyclic rings. Total synthesis of (+)-aspergillin PZ

Tetrahedron ◽

10.1016/j.tet.2011.09.079 ◽

2011 ◽

Vol 67 (51) ◽

pp. 9837-9843 ◽

Cited By ~ 28

Author(s):

Stephen M. Canham ◽

Larry E. Overman ◽

Paul S. Tanis

Keyword(s):

Total Synthesis ◽

Sigmatropic Rearrangement ◽

Aspergillin Pz

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