Diastereoselective Synthesis of Camptothecin‐like Scaffolds: Construction of a New Class of Pseudo‐natural Products

Author:

Srikanth Gourishetty1,Ravi Anil2,Sebastian Anusha2,Joseph Jobi2,Khanfar Monther A.3,El‐Gamal Mohammed I.24,Al‐Qawasmeh Raed A.3,Shehadi Ihsan A.3,McN. Sieburth Scott5,Abu‐Yousef Imad A.1,Majdalawieh Amin F.1,Al‐Tel Taleb H.24ORCID

Affiliation:

1. Department of Biology Chemistry and Environmental Sciences American University of Sharjah 26666 Sharjah United Arab Emirates

2. Sharjah Institute for Medical research University of Sharjah P.O. Box 27272 Sharjah United Arab Emirates

3. College of Science Department of Chemistry University of Sharjah 27272 Sharjah United Arab Emirates

4. College of Pharmacy University of Sharjah P.O. Box 27272 Sharjah United Arab Emirates

5. Department of Chemistry Temple University 201 Beury Hall 19122 Philadelphia PA USA

Abstract

AbstractThe discovery of novel small molecules endowed with high 3D‐content remains a powerful tool for interrogating underrepresented biological space. To this end, the pseudo‐natural products (pseudo‐NP) strategy has become one of the most important tools to deliver biologically significant chemical probes. In this article, we describe the development of a new class of pseudo‐NP collection, through connecting tryptamines with a furanose derivative followed by subjecting the product from this operation to a ring distortion strategy that led to diastereoselective synthesis of camptothecin‐like compounds. This process is driven by a cascade that unites Pictet–Spengler reaction with Michael addition reaction, followed by oxidative‐ring enlargement and subsequent transannular aldol cyclization delivering camptothecin‐like architectures. The obtained diastereoselectivity was verified using density functional theory (DFT) calculations.

Funder

University of Sharjah

American University of Sharjah

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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