Open AccessTotal Synthesis of (±)-Sceptrin
Author(s) -
Long Nguyen,
Timothy F. Jamison
Publication year - 2020
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.0c01381
Subject(s) - chemistry , cyclobutane , pyrrole , imidazole , natural product , intermolecular force , total synthesis , combinatorial chemistry , stereochemistry , organic chemistry , molecule , ring (chemistry)
A four-step synthesis of the dimeric pyrrole-imidazole alkaloid sceptrin is reported. The brevity of the route is based on a simple solution developed for selective assembly of the cyclobutane core of the natural product. The photochemical intermolecular [2 + 2] dimerization of a useful hymenidin surrogate enables direct entry to this enigmatic class of biologically active marine secondary metabolites.
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