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Total Synthesis of Two Possible Diastereomers of Natural 6‐Chlorotetrahydrofuran Acetogenin and Its Stereostructural Elucidation
Author(s) -
Takamura Hiroyoshi,
Katsube Tomoya,
Okamoto Kazuki,
Kadota Isao
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703234
Subject(s) - acetogenin , diastereomer , enyne , stereochemistry , total synthesis , natural product , chemistry , wittig reaction , stereoselectivity , absolute configuration , derivative (finance) , diene , annonaceae , organic chemistry , catalysis , biology , botany , financial economics , economics , natural rubber
The first total synthesis of two possible diastereomers of natural 6‐chlorotetrahydrofuran acetogenin 1 has been achieved. The synthetic route features 5‐ exo ‐ tet cyclization, Z selective Wittig reaction and Julia olefination for the construction of conjugated diene and enyne moieties, and stereoselective chlorination. Comparison of their 1 H and 13 C NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (−)‐6‐chlorotetrahydrofuran acetogenin 1 .