Takamura Hiroyoshi, Katsube Tomoya, Okamoto Kazuki, Kadota Isao
Department of Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.
Chemistry. 2017 Dec 6;23(68):17191-17194. doi: 10.1002/chem.201703234. Epub 2017 Nov 22.
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 H and C NMR data and specific rotation with those of the natural product elucidated the absolute configuration of natural (-)-6-chlorotetrahydrofuran acetogenin 1.
天然6-氯四氢呋喃产乙酸素1两种可能的非对映异构体的首次全合成已经实现。该合成路线的特点是通过5-外向-四环化、Z选择性维蒂希反应和朱利亚烯烃化反应构建共轭二烯和烯炔部分，并进行立体选择性氯化。通过将它们的氢谱和碳谱数据以及比旋光度与天然产物的数据进行比较，阐明了天然（-）-6-氯四氢呋喃产乙酸素1的绝对构型。
