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Synthesis 2023; 55(14): 2134-2142
DOI: 10.1055/a-2048-2662
DOI: 10.1055/a-2048-2662
paper
Studies Towards The Synthesis of Tartrolons D and E
This work was supported by the Science and Engineering Research Board (SERB), India through a Ramanujan Fellowship (D.O. No. SB/S2/RJN-071/2015). R.S. acknowledges a Department of Science and Technology, Innovation in Science Pursuit for Inspired Research (DST-INSPIRE) fellowship and M.R. acknowledges the Indian Institute of Science Education and Research Thiruvananthapuram (IISER-TVM) for an SRF fellowship.
Abstract
A concise and stereoselective synthesis of a key fragment C3-C22 unit of tartrolons D and E is demonstrated. Three crucial fragments are combined to form the 20-carbon chain, which contains four stereogenic centers in the monomeric unit of both natural products. The crucial fragments were synthesized in highly enantioselective routes from commercial starting compounds in two, eight, and two steps, respectively, and coupled using palladium-catalyzed Sonogashira coupling and directed 1,5-asymmetric aldol reaction as key steps.
Key words
macrodiolides - tartrolons - C3-C22 fragment - 1,5-asymmetric aldol - Sonogashira couplingSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2048-2662.
- Supporting Information
Publication History
Received: 17 January 2023
Accepted after revision: 06 March 2023
Accepted Manuscript online:
06 March 2023
Article published online:
13 April 2023
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See Supporting Information, Table [1].