Total synthesis of palau’amine

Kosuke Namba (), Kohei Takeuchi, Yukari Kaihara, Masataka Oda, Akira Nakayama, Atsushi Nakayama, Masahiro Yoshida and Keiji Tanino ()
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Kosuke Namba: Tokushima University
Kohei Takeuchi: Tokushima University
Yukari Kaihara: Faculty of Science, Hokkaido University
Masataka Oda: Graduate School of Medical and Dental Sciences, Niigata University
Akira Nakayama: Catalysis Research Center, Hokkaido University
Atsushi Nakayama: Tokushima University
Masahiro Yoshida: Tokushima University
Keiji Tanino: Faculty of Science, Hokkaido University

Nature Communications, 2015, vol. 6, issue 1, 1-9

Abstract: Abstract Palau’amine has received a great deal of attention in the past two decades as an attractive synthetic target by virtue of its intriguing molecular architecture and significant immunosuppressive activity. Here we report the total synthesis of palau’amine characterized by the construction of an ABDE tetracyclic ring core including a trans-bicylo[3.3.0]octane skeleton at a middle stage of total synthesis. The ABDE tetracyclic ring core is constructed by a cascade reaction of a cleavage of the N–N bond, including simultaneous formation of imine, the addition of amide anion to the resulting imine (D-ring formation) and the condensation of pyrrole with methyl ester (B-ring formation) in a single step. The synthetic palau’amine is confirmed to exhibit excellent immunosuppressive activity. The present synthetic route has the potential to help elucidate a pharmacophore as well as the mechanistic details of immunosuppressive activity.

Date: 2015
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DOI: 10.1038/ncomms9731

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