Total Synthesis of Two Possible Diastereomers of Natural 6‐Chlorotetrahydrofuran Acetogenin and Its Stereostructural Elucidation | Zendy

Takamura Hiroyoshi | Zendy; Katsube Tomoya | Zendy; Okamoto Kazuki | Zendy; Kadota Isao | Zendy

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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 .

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