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. 2013 Jun 7;69(36):7529-7550.
doi: 10.1016/j.tet.2013.06.004.

Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis

Paul A Wender  1
Affiliations

Toward the Ideal Synthesis and Transformative Therapies: The Roles of Step Economy and Function Oriented Synthesis

Paul A Wender. Tetrahedron. .
No abstract available

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Figures

Scheme 1
Scheme 1
Organo-bis-cuprates: New Reagents for a Single Step Spiroannelation
Scheme 2
Scheme 2
A Single Step Method for 7-membered Ring Synthesis based on a Divinylcyclopropane Rearrangement
Scheme 3
Scheme 3
An 11-step Synthesis of the Pseudoguaiane Damsinic Acid
Scheme 4
Scheme 4
A Photo-Thermal Olefin Metathesis Strategy: Total Synthesis of Isabelin
Scheme 5
Scheme 5
A Photo-Thermal Olefin Metathesis/Ene Cascade: Total Synthesis of Calameon.
Scheme 6
Scheme 6
Photo-Thermal Olefin Metathesis/Ene Sequence: Total Synthesis of Warburganal.
Scheme 7
Scheme 7
Macroexpansion Methodology: An 8-step Synthesis of 3Z-Cembrene A.
Scheme 8
Scheme 8
Macroexpansion Methodology: Synthesis of Muscone.
Scheme 9
Scheme 9
Diels-Alder/Cope Strategy for Hydroisoquinolines: 16-step Synthesis of Reserpine
Scheme 10
Scheme 10
The Arene-Alkene Meta-Photocycloaddition: A Unique, Complexity Increasing Strategy Level Reaction
Scheme 11
Scheme 11
The Arene-Alkene Meta-Photocycloaddition: A 4-Step Synthesis of Cedrene
Scheme 12
Scheme 12
A Template for Selectivity Predictions in Arene-Alkene Photocycloadditions
Scheme 13
Scheme 13
The Arene-Alkene Meta-Photocycloaddition: A 3-Step Synthesis of Silphinene
Scheme 14
Scheme 14
Representative Syntheses based on the Arene-Alkene Meta-Photocycloaddition
Scheme 15
Scheme 15
The First Intramolecular Metal Catalyzed [4+4] Cycloaddition
Scheme 16
Scheme 16
Intramolecular Metal Catalyzed [4+4] Cycloadditions: Synthesis of Asteriscanolide
Scheme 17
Scheme 17
Intramolecular Metal Catalyzed [4+4] Cycloadditions: Synthesis of Salsolene Oxide
Scheme 18
Scheme 18
A Photo[2+2]/Cope Sequence for 8-membered Rings: Formal Synthesis of Coriolin
Scheme 19
Scheme 19
Metal Catalyzed [4+2] Cycloadditions of Dienes and Alkynes
Scheme 20
Scheme 20
Metal Catalyzed [4+2] Cycloadditions of Dienes and Allenes.
Scheme 21
Scheme 21
Metal Catalyzed [4+2] Cycloadditions of Dienes and Alkynes: Steroid Synthesis
Scheme 22
Scheme 22
Metal Catalyzed [4+2] Cycloadditions: Yohimban Alkaloid Synthesis
Scheme 23
Scheme 23
Metal Catalyzed Multicomponent [m+n+o] Cycloadditions and Cascades
Scheme 24
Scheme 24
Metal Catalyzed Multicomponent [2+2+1], [4+2+1] and [4+2+2] Cycloadditions
Scheme 25
Scheme 25
Diverting a [4+2] Cycloaddition into Multicomponent [2+2+1] and [4+2+1] Cycloadditions
Scheme 26
Scheme 26
The Dienyl Pauson-Khand [2+2+1] Cycloaddition
Scheme 27
Scheme 27
An Alkyne Diverted [4+2] Reaction: A 3-Component [4+2+2] Cycloaddition
Scheme 28
Scheme 28
The Diene Effect: Diene-activated [2+2+1] Cycloadditions with Alkenes
Scheme 29
Scheme 29
The Diene Effect: Rare [2+2] and [2+2+2] Cycloadditions of Alkenes
Scheme 30
Scheme 30
The Diels-Alder [4+2] Cycloaddition as Inspiration for a New [5+2] Cycloaddition
Scheme 31
Scheme 31
Pi-directed Metal Catalyzed CC Bond Activation: Genesis of the [5+2] Cycloaddition
Scheme 32
Scheme 32
The First Metal Catalyzed [5+2] Cycloadditions
Scheme 33
Scheme 33
The First Intermolecular Metal Catalyzed [5+2] Cycloadditions
Scheme 34
Scheme 34
The First Metal Catalyzed [5+2] Cycloadditions: Synthesis of Dictamnol
Scheme 35
Scheme 35
The First Metal Catalyzed [5+2] Cycloadditions: Synthesis of Aphanamol
Scheme 36
Scheme 36
Diastereo- and Regio-control in CC Activation and Cycloaddition of VCPs
Scheme 37
Scheme 37
Substrate and Catalyst Control of Diastereo- and Regioselectivity
Scheme 38
Scheme 38
New Catalysts: Chiral, Water-Soluble, Cationic, and Carbene Catalysts
Scheme 39
Scheme 39
New Reactions beget New Reactions: Hetero [5+2] Cycloadditions and [6+2] and [6+1] Cycloadditions
Scheme 40
Scheme 40
A New 3-Component [5+2+1] Reaction for 8-membered Ring and Diquinane Synthesis
Scheme 41
Scheme 41
[5+2]/[4+2] Cascades: A One-Step, Scalable Route to Kinase Inhibitors
Scheme 42
Scheme 42
Cascade Catalysis: The Metal Catalyzed [5+2]/Metal Catalyzed Nazarov Cascade
Scheme 43
Scheme 43
Connectivity Analysis (COANAN): A Chemically Unbiased Graph Theoretical Approach to Identifying Preferred Complexity Increasing, Step Economical Strategies
Scheme 44
Scheme 44
The Pinene Path to Taxol Analogs: 5-Steps to the Homo-Chiral Taxane Tricyclic Core
Scheme 45
Scheme 45
The Pinene Path: Total Synthesis of Taxol
Scheme 46
Scheme 46
Oxido-Pyrylium [5+2] Cycloadditions: The Total Synthesis of Phorbol
Scheme 47
Scheme 47
Oxido-Pyrylium [5+2] Cycloadditions: The Total Synthesis of Resiniferatoxin
Scheme 48
Scheme 48
Oxido-Pyrylium [5+2] Cycloadditions: Synthesis of Des-epoxy-Yuanhuapin, a Gateway Strategy for accessing Diterpene Orthoesters
Scheme 49
Scheme 49
Leads for HIV/AIDS Eradication: Semi-synthesis of Prostatin and its Analogs
Scheme 50
Scheme 50
Function Oriented Synthesis: Step Economy and Superior Function by Design
Scheme 51
Scheme 51
Function Oriented Synthesis: Designed Dynemicin Analogs
Scheme 52
Scheme 52
FOS Designed Photonucleases cleave DNA: Light Activatable DNA Cleavage
Scheme 53
Scheme 53
FOS Designed Triazole Photonucleases cleave DNA: Light Activatable DNA Cleavage
Scheme 54
Scheme 54
FOS Designed Photonucleases with DNA Recognition Elements Selectively Cleave DNA
Scheme 55
Scheme 55
Translating Nature’s Library: Computer Assisted Design of the First Bryostatin Analogs (Bryologs)
Scheme 56
Scheme 56
FOS: The First Designed Bryostatin Analogs – Step Economical Synthesis and Superior Function
Scheme 57
Scheme 57
FOS and New Methodology: The Prins-Driven Macrocyclization
Scheme 58
Scheme 58
FOS and New Methodology: End Stage in the Total Synthesis of Bryostatin 9
Scheme 59
Scheme 59
Lead Diversification through A Prins-Driven Macrocyclization/Nucleophile, Ritter or Friedel-Crafts Cascade
Scheme 60
Scheme 60
Nature Inspired Guanidinium-rich Cell Penetrating Molecular Transporters
Scheme 61
Scheme 61
FOS and the Design and Development of Guanidinium-Rich Cell Penetrating Molecular Transporters
Scheme 62
Scheme 62
Organocatalytic Oligomerizations: A One Step Synthesis of Biodegradable Transporters for siRNA Delivery into Cells
Scheme 63
Scheme 63
Taxol Transporter Conjugates Overcome Taxol Resistance in Cells, in Animals and in ex vivo Samples of Ovarian Cancer Patients
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References

    1. Kornberg A. Biochemistry. 1987;26:6888–6891. - PubMed

    1. October Sky. Dir. Joe Johnson. Perf. Jake Gyllenhaal, Chris Cooper, Laura Dern. Universal Pictures, 1999. DVD. A 1999 film about a coal miner’s son, inspired by rocket science of the time, and not dissimilar from my own experiences and that of many others.

    1. Wender PA, Miller BL. Toward the Ideal Synthesis: Connectivity Analysis and Multi-Bond Forming Processes. In: Hudlicky T, editor. In Organic Synthesis: Theory & Applications. Vol. 2. JAI; Greenwich, CT: 1993. pp. 27–66.
    2. Wender PA. Introduction: Frontiers in Organic Synthesis. Chemical Reviews. 1996;96(1) Editorial. - PubMed
    3. Wender PA, Wright D, Handy S. Toward the Ideal Synthesis. Chemistry & Industry. 1997;19:767–769.
    4. Wender PA, Verma VA, Paxton TJ, Pillow TH. Function Oriented Synthesis, Step Economy, and Drug Design. Accts Chem Res. 2008;41:40–49. - PubMed
    5. Wender PA, Miller BL. Synthesis at the Molecular Frontier. Nature. 2009;460:197–201. - PMC - PubMed
    1. Wender PA, Ternansky RJ. Tetrahedron Lett. 1985;26:2625–2628.
    1. Wender PA, Howbert JJ. J Am Chem Soc. 1981;103:688–689.

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