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Total Synthesis of Homodimericin A
Author(s) -
Feng Juan,
Lei Xiaoqiang,
Guo Zhen,
Tang Yefeng
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201702893
Subject(s) - chemistry , tandem , hydroquinone , stereochemistry , tricyclic , total synthesis , structural motif , monomer , organic chemistry , materials science , biochemistry , composite material , polymer
We report the concise total synthesis of homodimericin A ( 1 ), a recently identified fungal metabolite bearing an unprecedented molecular architecture. The success of the approach hinges on a series of rationally designed and bioinspired transformations, including a Moore rearrangement to assemble the monomeric hydroquinone precursor, homodimerization through double Michael addition to construct the planar A/B/C tricyclic framework, and a tandem Diels–Alder reaction/carbonyl–ene cyclization to forge the congested D/E/F tricyclic cage motif. Unequivocal evidence for the elucidated structure of homodimericin A was also provided by this study.