Abstract
Grignard coupling of isopropylmagnesium bromide with 4-(tetrahydropyranyloxy)bromobutane (2) and subsequent bromination gave 4. Alkylation of 1-(tetrahydropyranyloxy)undec-10-yne (5) with 4 and 1-bromohexane, acidic hydrolysis, and bromination furnished halogenoalkynes 7 and 9, respectively. Likewise, coupling of isobutyl magnesium bromide with 12-(tetrahydropyranyloxy)bromododecane (12) followed by bromination afforded 1-halogenoalkane 14. Alkylation of 1-(tetrahydropyranyloxy)-2-propyne (15) with 7, 9, and 14 and oxidation of the respective products afforded the alkynals 16a-c. These on reaction with lithium acetylide and subsequent chemoselective trans reduction of the internal alkynes led to the target compounds alk-4-en-1-yn-3-ols I-III
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