Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 23, Pages 15118-15130Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02066
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Funding
- Finnish Centre of Excellence in Molecular Biology of Primary Producers (Academy of Finland CoE programme) [271832]
- Gatsby Foundation [GAT3395/PR3]
- University of Helsinki [799992091]
- European Research Council [323052]
- National Science Foundation Biotechnology and Biological Sciences Research Council [BB/N013158/1]
- European Research Council (ERC) [323052] Funding Source: European Research Council (ERC)
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Orthogonally protected polyamines (PAs) have been synthesized using alpha,omega-diamines and omega-aminoalcohols as N-C-x-N and N-C-y synthons, respectively, and the Mitsunobu reaction as the key reaction for the assembly of the PA skeleta. The Trt, Dde, and Phth groups have been employed for protecting the primary amino functions and the Ns group for activating the primary amino functions toward alkylation and secondary amino function protection. The approach has been readily extended to accommodate the total synthesis of the spider toxins Agel 416 and HO-416b, incorporating the 3-4-3-3 and the 3-3-3-4 PA skeleton, respectively.
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