An alternative synthetic route to the C(11)-C(17)-fragment of mycinolide IV

Katsuhiko Tomooka, Kazutsugu Matsumoto, Keisuke Suzuki, Gen Ichi Tsuchihashi

研究成果: ジャーナルへの寄稿記事

1 引用 (Scopus)

抄録

An efficient chiral synthesis of (4R,5R)-4-(4-methoxybenzyloxymethyl)-2-heptene-1,5-diol (4), which corresponds to the C(11)-C(17) segment of mycinolide IV (1), is described. One of the key steps is the asymmetric pinacol-type rearrangement of a chiral glycerol-derived mesylate 12, promoted by a modified organoaluminum reagent (1:1 mixture of trimethylaluminium and diethyl ether). Stereospecific 1,2-shift of a three-carbon alkenyl group gave (R)-4-(4-methoxybenzyloxymethyl)-5-trimethylsilyl-7-(2-trimethylsilylethoxymethoxy)-5-hepten-3-one (13) 80 % yield. Reduction of 13 with lithium triethylborohydride followed by removal of silyl groups gave 4 in enantio- and diastereomerically pure form.

元の言語英語
ページ(範囲)129-130
ページ数2
ジャーナルSynlett
1992
発行部数2
DOI
出版物ステータス出版済み - 2 1 1992

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Mesylates
Lithium
Ether
Glycerol
Carbon
mycinolide IV

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

これを引用

An alternative synthetic route to the C(11)-C(17)-fragment of mycinolide IV. / Tomooka, Katsuhiko; Matsumoto, Kazutsugu; Suzuki, Keisuke; Tsuchihashi, Gen Ichi.

:: Synlett, 巻 1992, 番号 2, 01.02.1992, p. 129-130.

研究成果: ジャーナルへの寄稿記事

Tomooka, K, Matsumoto, K, Suzuki, K & Tsuchihashi, GI 1992, 'An alternative synthetic route to the C(11)-C(17)-fragment of mycinolide IV', Synlett, 巻. 1992, 番号 2, pp. 129-130. https://doi.org/10.1055/s-1992-21289
Tomooka, Katsuhiko ; Matsumoto, Kazutsugu ; Suzuki, Keisuke ; Tsuchihashi, Gen Ichi. / An alternative synthetic route to the C(11)-C(17)-fragment of mycinolide IV. :: Synlett. 1992 ; 巻 1992, 番号 2. pp. 129-130.
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