Scribd
Upload
11 views30 pages

Presentation Template 1 1 (Auto-Saved)

The document discusses an enantioselective organocatalytic cascade for synthesizing pyrroloindolines, highlighting its advantages over traditional methods, such as improved yields, reduced steps, and environmental friendliness. It details the catalytic cycle involved, the synthesis of natural products, and the challenges faced in achieving high stereoselectivity. The method is noted for its efficiency, allowing access to a variety of natural products while minimizing waste.

Uploaded by

sanganideep11
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
11 views30 pages

Presentation Template 1 1 (Auto-Saved)

The document discusses an enantioselective organocatalytic cascade for synthesizing pyrroloindolines, highlighting its advantages over traditional methods, such as improved yields, reduced steps, and environmental friendliness. It details the catalytic cycle involved, the synthesis of natural products, and the challenges faced in achieving high stereoselectivity. The method is noted for its efficiency, allowing access to a variety of natural products while minimizing waste.

Uploaded by

sanganideep11
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
You are on page 1/ 30

An Enantioselective Organocatalytic Cascade for the

synthesis of Pyrroloindolines

• Mahadik Roshan Eknath Irene • Pratibha Sontakke


• Sangani Deepkumar Umeshbhai • Shafna TT
• Ayesha • Fathima Shifana P
• Anantha Hari H • S Swathi
• Akshay Kumar • Aditya Deo
• Mohit Thakre • Priyadharshini K
• Soumyadip Bank

1
 What is an organocatalytic cascade?
Introduction

 Why is it preferred over other cascades?

 What is the product being synthesized?

 Where is it used?

 Why this method?

 How does enantioselectivity arise?

2
Introduction

Organocatalytic Cascade: Uses organic molecules as a


catalyst in a cascade reaction

Nature of catalyst chosen is according to


the nature of substrate More environmentally friendly, lower
Can be acidic, basic, nucleophilic, toxicity
electrophilic

Chiral molecules give enantioselective


Works with most organic solvent
products

3
Why this Cascade?

Our Target Molecule

B C

N
Me
N H
H
David MacMillan

4
Why this Cascade?

Synthesis of Pyrolloindoline ring gives access to many natural products with high
stereoselectivity

5
Why this Cascade?

Synthesis of Pyrolloindoline ring gives access to many natural products with high
stereoselectivity

6
Why this Cascade?

B C
Mild Reaction conditions
A -40° C, Organic Solvents, HX

N
Me High Yields and selectivity
N H (66-99 % Yields with >80% ee)
H

Challenges
Synthesis of Furanoindoline rings
Quarternary stereocenter-C by modification of starting material
Diastereocontrol
Pyrroloindoline ring system
Commercially available catalyst
Enantioselective Catalysis
and starting materials
Buy this catalyst

7
Catalyst + α,β
unsaturated
Introduction aldehyde

Hydrolysis to
regenerate Formation of
Catalytic Cycle catalyst and Iminium Ion
product

Bond formation
Ring closing to with Indole at β
give Position of
pyrolloindoline indole

8
Catalytic Cycle

9
Synthesis of Natural Products

Natural Products Synthesised using this cascade

10
Synthesis of Natural Products

Natural Products Synthesised using this cascade

8 Step synthesis reduced to 5 steps

5 11
Synthesis of Natural Products

Many Natural Products Synthesised using this


cascade

From 31 steps to 9 steps

4, 12
Why this Cascade?

13
Introduction Good yields and atom economy Reduction in waste

Catalytic Cycle Avoids toxic and harsh reaction Access to a library of natural
conditions products

Conclusions Ready access to starting


Reduction in synthesis steps
materials

All in all, a great cascade !!!

14
References

1. Austin JF, MacMillan DW. Enantioselective organocatalytic indole alkylations. Design of a


new and highly effective chiral amine for iminium catalysis. J Am Chem Soc. 2002 Feb
20;124(7):1172-3. doi: 10.1021/ja017255c. PMID: 11841277.
2. Nine-Step Enantioselective Total Synthesis of (-)-Vincorine. Benjamin D. Horning and David
W. C. MacMillan. J. Am. Chem. Soc. 2013, 135, 17, 6442–6445.
3. Enantioselective Organo-Cascade Catalysis. J. Am. Chem. Soc. 2005, 127, 43, 15051–
15053.
4. Total Synthesis of the Akuammiline Alkaloid (±)-Vincorine, Min Zhang, Xiaoping Huang,
Liqun Shen, and Yong Qin, Journal of the American Chemical Society 2009 131 (16), 6013-
6020 DOI: 10.1021/ja901219v
5. Kawasaki, T.; Shinada, M.; Kamimura, D.; Ohzono, M.; Ogawa, A. Enantioselective Total
Synthesis of (−)-Flustramines A, B and (−)-Flustramides A, B via Domino
Olefination/Isomerization/Claisen Rearrangement Sequence. Chem. Commun. 2006, No. 4,
420–422. https://doi.org/10.1039/b512485a.

15
Thank You

16
Supporting Information

19
Supporting Information

20
Supporting Information

21
Supporting Information

22
Supporting Information

23
Supporting Information

24
Supporting Information

25
Supporting Information

26
Supporting Information

27
Supporting Information

28
Supporting Information

29
Supporting Information

30

You might also like