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Total syntheses of Metacridamide B, Strasseriolide A, Chondrochloren A and Thermolide E using Füstner/ Micalizio as key reactions

Implementing Organization

Institute of Chemical Technology
Principal Investigator
Dr. Subash Ghosh
CSIR - Indian Institute Of Chemical Technology, Maharashtra

Project Overview

2-methylprop-2-en-1-ol is a structural unit present in various natural products having complex structure as well as important biological activity. This important unit can be synthesized by two elegant methodologies developed by Fustner and Micalizio. Addition of 3-substituted propyne to an aldehyde or addition of 2-substituted alkyne to an aldehyde followed by hydroxyl directed functionalization of the resulting propargylic alcohol creates 2-methylprop-2-en-1-ol unit. Recently we have utilized these two important methodologies for the synthesis of the proposed structure of Metacridamides B and found that the structure of the molecule has been reported wrongly. Therefore in this proposal the total synthesis of the actual natural product Metacridamide B will be undertaken using the strategy developed for the proposed structure of Metacridamide B. The developed strategy will be further extended to the total synthesis of other two important natural products namely Strasseriolide A, Chondrochloren A. Further it has been realized that the hydrogenation of 2-methylprop-2-en-1-ol under suitable chiral catalyst would provide diastereomerically pure 1,3-dimethyl propanol unit that is present in various natural products and this strategy will be utilized for the total synthesis of architecturally complex and biologically important natural product Thermolide E.

Source

Source
Science and Engineering Research Board (SERB), DST 2022-23
Funding Organization
Funding Organization
Science and Engineering Research Board (SERB), New Delhi
Quick Information
Area of Research
Chemical Sciences
Start Date
2022
End Date
2025
Status
Completed
Contact
subhash@iict.res.in
Output
No. of Research Paper
00
Technologies (If Any)
00
No. of PhD Produced
00
Publications
00
No. of Patents
Filed : 00
Grant : 00
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