The following sequence of reactions was employed during a synthesis of the sex pheromone
Chapter 12, Problem 12.41(choose chapter or problem)
The following sequence of reactions was employed during a synthesis of the sex pheromone of the dermestid beetle (Tetrahedron 1977, 33, 24472450). The conversion of compound 5 to compound 6 involves the removal of the THP group (ROTHP S ROH), which is accomplished in acidic conditions (TsOH). Provide the structures of compounds 2, 4, 5, 6, and 7: BH3 THF 1 1) Br2 2) NaOMe Br HC CLi DMSO 1) BuLi 2 2) I(CH2) 7OTHP 6 2-Tetrahydropyranyl TsOH MeOH 5 7 3 H2 Pd/BaSO4 MeOH quinoline 4 O THP
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