A tandem denitration-deoxygenation of .alpha.-nitro ketones via (p-tolylsulfonyl)hydrazones with lithium aluminum hydride: a practical synthesis of (Z)-9-tricosene, the sex pheromone of the housefly (Musca domestica)

Asymmetric Synthesis of Highly Substituted β-Nitro Alcohols and Enantiomerically Enriched 4,4,5-Trisubstituted Oxazolidinones

“…4-Methyl-4-nitro-1-phenyl-3-pentanone (5). Following the general procedure, (±)- 12 (1.90 g, 8.5 mmol) afforded 5 (1.56 g, 83%) as a colorless oil. IR (film, cm -1 ) ν 1728, 1543; 1 H NMR δ 7.28−7.14 (m, 5H), 2.93 (t, J = 7.2 Hz, 2H), 2.80 (t, J = 6.5 Hz, 2H), 1.66 (s, 6H); 13 C NMR δ 201.2, 128.7, 128.7, 128.4, 128.4, 128.3, 126.5, 38.5, 29.9, 23.1.…”

Syntheses of Insect Sex Pheromones. A Review of the Literature 1990-1998

“…The subsequent tandem denitration-deoxygenation afforded 2.6. A practical synthesis of (Z)-tricos-9-ene, sex pheromone of the housefly (Musca domestica), was based on a similar principle 16 .…”

“…Extending the series of stereospecific syntheses described earlier (see, e.g., refs 118,119 ), Odinokov et al 120 performed synthesis of (7Z,11E)-hexadeca-7,11-dien-1-yl acetate (7.88) (Scheme 52). Cross-coupling of two eight-carbon units, namely that of 8-(tetrahydropyranyloxy)oct-1-yne (7.76; prepared from diol 7.77) and of (3E)-oct-3-enyl bromide (7.78; prepared from hexanal (7.80) via (3E)-oct-3-enoic acid (7.79)), gave the C 16 (11Z)-Hexadec-11-en-1-ol, its acetate and the corresponding aldehyde (7.90, 7.91 and 7.92, respectively) the pheromone components of Mamestra and Heliothis sp., were synthesized by Odinokov et al 123 124 in the synthesis of (5Z)-dec-5-en-1-yl acetate (7.98), the pheromone of the moths of Agrotis sp. In this synthesis (Scheme 54), the ester 7.96 reacted with pentyltriphenylphosphonium ylide to give 7.97 (R = CH 3 (CH 2 ) 4 ) which, on reduction and acetylation, furnished the acetate 7.98.…”

“…The analogs 8.18 were obtained from 8. 16 Fukusaki et al 152 prepared (5Z)-5-(oct-1-en-1-yl)tetrahydrofuran-2-one (8.23), a sex pheromone of the cupreous chafer beetle. This compound is structurally close to the Japanese beetle pheromone (the side chain is by two carbon atoms longer) and the unnatural enantiomer was assumed to be a pheromone inhibitor.…”

α-Nitro Ketone Synthesis Using N-Acylbenzotriazoles

“…The nitro group in these versatile building blocks can readily be reduced with retention of configuration, and the resulting amino alcohols are key intermediates in the construction of numerous pharmacologically important compounds , and chiral auxiliaries . Additionally, α-nitro ketones are valuable precursors for the syntheses of many classes of natural products including jasmonoids and prostaglandin intermediates 1a and pheromones …”