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

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

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)129-130
Number of pages2
JournalSynlett
Volume1992
Issue number2
DOIs
Publication statusPublished - Feb 1 1992
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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