Synthesis of racemic 6,10,14-trimethylpentadecan-2-ol, a pheromone of rice moth and 5,9,13-trimethyltetradecanoic acid, a component of marine sponge from a common intermediate.
A facile synthesis of dl-6,10,14-trimethylpentadecan-2-ol (1) a pheromone component of rice moth, Corcyra cephalonica Stainton and 5,9,13-trimethyltetradecanoic acid (2) a component of marine sponge, Cinachyrella alloclada Uliczka, using a common, intermediate, hexahydrofarnesol is accomplished. The salient features for 1 are: Grignard coupling of 5 with allylmagnesium bromide and oxymercuration-demercuration whereas for 2 they are: Knoevenagel condensation and subsequent hydrogenation.
Rane
S S
SS
Bioorganic Division, Bhabha Atomic Research Centre, Bombay, India.
Chadha
M S
MS
Mamdapur
V R
VR
D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D000818:Animals; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009036:Moths / Q000737:chemistry*; D010675:Pheromones / Q000138:chemical synthesis* / Q000737:chemistry; D011161:Porifera / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D000438:Alcohols; D005227:Fatty Acids; D010675:Pheromones; D013729:Terpenes; C089468:5,9,13-trimethyltetradecanoic acid; C089467:6,10,14-trimethylpentadecan-2-ol