✦ LIBER ✦
ChemInform Abstract: Base-Induced Rearrangement of Perhydronaphthalene-1,4-diol Monosulfonate Esters to 11-Oxatricyclo[5.3.1.02,6]undecanes. Total Synthesis of Furanether B.
✍ Scribed by R. P. L. BELL; A. SOBOLEV; J. B. P. A. WIJNBERG; A. GROOT
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 42 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Base-Induced
Rearrangement of Perhydronaphthalene-1,4-diol Monosulfonate Esters to 11-Oxatricyclo[5.3.1.0 2,6 ]undecanes. Total Synthesis of Furanether B.
-In the presence of LiAlH(O-tBu) 3 the mesylate (I) is found to undergo selective rearrangement to the tricyclic derivative (II). This rearrangement is one key step in the synthesis of furanether B (IX). The other key step is the Pummerer-induced cyclization toward the lactaranolides (VII) and (VIII). -(BELL, R.