The Enantioselective Synthesis of Marmelo Oxides A and B and the Assignment of the Absolute Configurations of Marmelo Oxides

Syntheses of Chiralγ-Lactones fromd-andl-Arabinoses

“…3. Unexpectedly, 13,15,17,18) the geometry of the rx,j3-unsaturated esters ( -)-2a and ( -)-2b were assigned exclusively as Z; the coupling constant, 3J H2 ,H3 of (-)-2a was 11.2Hz, which should be assignable 19 ) to be Z although the stabilized ylide is known to preferentially give the …”

Monoterpenoids

“…The epoxidation of geraniol (22) by rn-chloroperoxybenzoic acid in a water-organic emulsion leads to the oxirane (50) with 98-100 YO selectivity. *' Nerol (25) behaves similarly. Both geraniol and nerol are oxidized by RuO, .…”

“…68 The optimum conditions for production of citronella1 (23) from Cyrnbopogon winterianus Jowitt have been as has the availability of citronellol(24) from various Geranium hybrids." An analysis of Turkish rose oil has revealed that its main constituents are citronellol (24) and nerol (25). 71 The…”

“…The ocimene (20) reacts with ROH and HMPA and [(MeCN),PdCl,] to give the (~3-allyl)palladium species (43). Treatment of (43) with a base leads to a mixture of geraniol (22), isogeraniol (44), and citral (36).85 Myrcene (21) undergoes a similar series of reactions to give nerol (25) and citral (36). The reaction of myrcene (21) with methyl acrylate, catalysed by a cobalt complex, leads to a mixture of the (2)-and (E)isomers of the esters (45) and (46).86 Photolysis of myrcene in the presence of a catalytic quantity of CF,SO,Cu yields the cyclized product (47).…”

Application of the Benzoate Chirality Method for γ-Lactones with Unsaturation at the C5 PositionviaAcyclic Allylic Alcohols, and Confirmation of the Absolute Configurations of Japanese Beetle’s Sex Pheromone and Marmelo Lactones

“…NaHC0 3 and water. After drying over MgS0 4 , the solvent was evaporated in vacuo to give a crude syrup of 6, which was purified by preparative TLC developing with n-hexane-ethyl acetate Similar to the preparation of 5 or 6,· the compounds 7,....., 11 were prepared from the corresponding y-Iactones 14 ) and identified by IR, UV and 1 H -NMR spectra. …”