The Floral Odour of Pelt’ndra Virgznica Contains Novel Trimethyl-2,5-dioxabicyclo[3.2.1]nonanes
نویسنده
چکیده
The qualitative and quantitative composition of the floral odour of Peltandra uirginica was determined by trapping odour components from freshly cut inflorescences on Tenax and Carbotrap adsorbents using a purge and trap apparatus. Analysis showed that a single novel compound, 1,3,6-trimethyl-2,5-dioxabicyclo[3.2.l.]nonane, comprised nearly 70% of the odour. Four isomers of this compound were found in much smaller amounts (l&7.6%) while an analogue with m, 142 comprised 13% of the odour. Small amounts (ca 0.3-2.5%) of two isomers of methylundecene and three isomers of dimethyldodecenone were also detected. This is the first case of trimethyldioxabicyclo[3,2,l]nonanes reported in floral odours.
منابع مشابه
Synthesis of the C8’-epimeric thymine pyranosyl amino acid core of amipurimycin
The C8'-epimeric pyranosyl amino acid core 2 of amipurimycin was synthesized from D-glucose derived alcohol 3 in 13 steps and 14% overall yield. Thus, the Sharpless asymmetric epoxidation of allyl alcohol 7 followed by trimethyl borate mediated regio-selective oxirane ring opening with azide, afforded azido diol 10. The acid-catalyzed 1,2-acetonide ring opening in 10 concomitantly led to the fo...
متن کاملGolgi-modifying properties of macfarlandin E and the synthesis and evaluation of its 2,7-dioxabicyclo[3.2.1]octan-3-one core.
Golgi-modifying properties of the spongian diterpene macfarlandin E (MacE) and a synthetic analog, t-Bu-MacE, containing its 2,7-dioxabicyclo[3.2.1]octan-3-one moiety are reported. Natural product screening efforts identified MacE as inducing a novel morphological change in Golgi structure defined by ribbon fragmentation with maintenance of the resulting Golgi fragments in the pericentriolar re...
متن کاملPalladium-catalysed cyclisation of alkenols: Synthesis of oxaheterocycles as core intermediates of natural compounds
The study of Pd-catalysed cyclisation reactions of alkenols using different catalytic systems is reported. These transformations affect the stereoselective construction of mono- and/or bicyclic oxaheterocyclic derivatives depending on a starting alkenol. The substrate scope and proposed mechanism of Pd-catalysed cyclisation reactions are also discussed. Moreover, the diastereoselective Pd-catal...
متن کاملDivergent synthesis and chemical reactivity of bicyclic lactone fragments of complex rearranged spongian diterpenes.
The synthesis and direct comparison of the chemical reactivity of the two highly oxidized bicyclic lactone fragments found in rearranged spongian diterpenes (8-substituted 6-acetoxy-2,7-dioxabicyclo[3.2.1]octan-3-one and 6-substituted 7-acetoxy-2,8-dioxabicyclo[3.3.0]octan-3-one) are reported. Details of the first synthesis of the 6-acetoxy-2,7-dioxabicyclo[3.2.1]octan-3-one ring system, includ...
متن کاملTiCl4 catalyzed tandem construction of C-C and C-O bonds: a simple and one-pot atom-economical stereoselective synthesis of spiro-oxindoles.
An atom-economical stereoselective synthesis of [{1-acetyl-5-methyl-6,8-dioxabicyclo(3.2.1)octane}-7-spiro-3'-(indolin-2'-one)] derivatives, containing both the oxindole and 6,8-dioxabicyclo(3.2.1)octane moieties via TiCl(4) catalyzed coupling of 2-acetyl-6-methyl-2,3-dihydro-4H-pyran with isatin derivatives is described.
متن کامل