149115-62-8

Upstream product

• 38049-10-4 ethyl 5-oxo-6-heptenoate 
• 100-42-5 styrene 
• 199286-33-4 (R)-6-vinyltetrahydropyran-2-one 
• 160226-44-8 (R)-(-)-γ-Hydroxymethyl-δ-valerolactone 
• 1224-56-2 tributylbenzylphosphonium chloride 
• 160154-84-7 (R)-5-formyl δ-valerolactone 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 33407-50-0 (E)-5-oxo-7-phenylhept-6-enoic acid 

Downstream Products

• 136685-37-5 (1R,5R,7S,8S)-8-hydroxy-7-phenyl-2,6-dioxa-bicyclo-[3.3.1]-nonan-3-one 
• 22639-28-7 (R)-goniothalamin 

Relevant academic research and scientific papers

Synthesis and cytotoxic activities of goniothalamins and derivatives

Substituted goniothalamins containing cyclopropane-groups were efficiently prepared in high yields and good selectivity. Antiproliferative activity was measured on three human cancer cell lines (A549, MCF-7, HBL-100), to show which of the structural elements of goniothalamins is mandatory for cytotoxicity. We found that the configuration of the stereogenic centre of the δ-lactone plays an important role for cytotoxicity. In our studies only (R)-configured goniothalamins showed antiproliferative activity, whereby (R)-configuration accords to natural goniothalamin (R)-1. Additionally, the δ-lactone needs to be unsaturated whereas our results show that the vinylic double bond is not mandatory for cytotoxicity. Furthermore, with a two-fold in vitro and in vivo strategy, we determined the inhibitory effect of the compounds to the yeast protein Pdr5. Here, we clearly demonstrate that the configuration seems to be of minor influence, only, while the nature of the substituent of the phenyl ring is of prime importance.

Alcohol dehydrogenase-catalyzed synthesis of enantiomerically pure δ-lactones as versatile intermediates for natural product synthesis

Starting from ethyl 4-bromobutyrate, the chemoenzymatic synthesis of 6-vinyl-tetrahydro-pyran-2-one has been accomplished. A screening of a number of available alcohol dehydrogenases and intense optimization of reaction parameters enabled us to establish an efficient synthesis of either enantiomer of the vinyllactone with excellent enantiomeric excess (>99%). The scope of possible applications of enantiopure vinyllactones has been verified by subjection to cross-metathesis resulting in the total synthesis of the insect pheromone (S)-5-hexadecanolide and the cytotoxic styryllactone goniothalamine as well as derivatives thereof. Copyright

Efficient synthesis of the styryllactones, (+)-goniothalamin, (+)-7-epi-goniodiol and (+)-9-deoxygoniopypyrone

An efficient synthesis of (+)-goniothalamin is described with aldehyde 4 as the key intermediate; the absolute configuration of (+)-7-epi-goniodiol was determined through its asymmetric synthesis from (+)-goniothalamin and, based on the conformation analysis of the four dihydroxylated isomers of (+)-goniothalamin, it can be concluded that the absolute configuration of the hydroxy at C8 determines the forms in nature.

Baker's yeast reduction of arylalkyl and arylalkenil γ- and δ-keto acids

γ- and δ-Lactones 5, 6, 13, 14, 15 and 16 were synthesized via baker's yeast reduction of the corresponding keto acids 3, 4 and 9-12. The enantioselectivity of the reduction is strongly dependent on the nature of the keto acid; the δ-lactones ware always obtained in an ee% higher than the γ-lactones and ranging from 70% to 100%.