title: First total synthesis of acetylenic alcohol 15-methyltricosa-2,4-diyne-1, 6-diol (strongylodiol-G) derived from marine sponge.
abstract: The first total and efficient synthesis of a naturally occurring acetylenic alcohol 15-methyltricosa-2,4-diyne-1,6-diol (strongylodiol-G) derived from marine sponge involving nine steps has been described. 1-Bromo-9-methyloctadecane (5) and hex-6-tetrahydropyranyloxyhex-2,4-diyn-1-al (9) which were initially synthesised separately starting from 1,8-octanediol (1) and propargyl alcohol (6), respectively, have been used as the final intermediates to obtain the title compound. The key steps in the synthesis involved ionic liquid-mediated bromination of 1,8-octanediol (1), tetrahydropyranylation of 8-bromooctan-1-ol (2) using acidic ionic liquid [bmim]HSO4 and monotetrahydropyranylation of hex-2,4-yn-1,6-diol (7) using ultrasonic energy.
authors.affiliation: a Department of Chemistry and Centre of Advanced Studies in Chemistry , Panjab University , Chandigarh , India.
authors.forename: Neeraj
authors.initials: N
authors.lastname: Gupta
authors.lastname: Shallu
authors.forename: Goverdhan Lal
authors.initials: GL
authors.lastname: Kad
authors.forename: Jasvinder
authors.initials: J
authors.lastname: Singh
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D008386:Marine Biology; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C000591440:15-methyltricosa-2,4-diyne-1,6-diol; D000438:Alcohols; D000480:Alkynes; D020005:Propanols; C572476:acetylenic alcohol; C028255:propargyl alcohol