24190-34-9Relevant academic research and scientific papers
Preparation of oxocene terpenes. the first enantiospecific synthesis of cytotoxic arenaran A
Torres, Alejandro,Gutierrez, Pilar,Alvarez-Manzaneda, Ramón,Chahboun, Rachid,Alvarez-Manzaneda, Enrique
, p. 9836 - 9845 (2016)
The first syntheses of cytotoxic marine arenarans A and B starting from commercial (-)-sclareol are reported. The oxocene ring of the target compound is formed via ring-closing metathesis, a process that depends on certain structural requirements. The tra
NIS-PPh3: A selective reagent for the spiroannulation of o-allyl phenols. total synthesis of corallidictyal D
Cano, M. Jose,Bouanou, Hanane,Tapia, Ruben,Alvarez, Esteban,Alvarez-Manzaneda, Ramon,Chahboun, Rachid,Alvarez-Manzaneda, Enrique
, p. 9196 - 9204 (2013)
Treatment of o-allyl phenols with catalytic NIS-PPh3 affords the corresponding spirodihydrobenzofuran derivatives in high yield with high regio- and total stereoselectivity under mild conditions. These results were utilized to achieve the first
Asymmetric Cation-Olefin Monocyclization by Engineered Squalene–Hopene Cyclases
Aeberli, Natalie,Berweger, Raphael,Bornscheuer, Uwe T.,Buller, Rebecca,Dossenbach, Sandro,Eichenberger, Michael,Eichhorn, Eric,Flachsmann, Felix,Hüppi, Sean,Hortencio, Lucas,Patsch, David,Voirol, Francis,Vollenweider, Sabine
, p. 26080 - 26086 (2021/09/20)
Squalene–hopene cyclases (SHCs) have great potential for the industrial synthesis of enantiopure cyclic terpenoids. A limitation of SHC catalysis has been the enzymes’ strict (S)-enantioselectivity at the stereocenter formed after the first cyclization step. To gain enantio-complementary access to valuable monocyclic terpenoids, an SHC-wild-type library including 18 novel homologs was set up. A previously not described SHC (AciSHC) was found to synthesize small amounts of monocyclic (R)-γ-dihydroionone from (E/Z)-geranylacetone. Using enzyme and process optimization, the conversion to the desired product was increased to 79 %. Notably, analyzed AciSHC variants could finely differentiate between the geometric geranylacetone isomers: While the (Z)-isomer yielded the desired monocyclic (R)-γ-dihydroionone (>99 % ee), the (E)-isomer was converted to the (S,S)-bicyclic ether (>95 % ee). Applying the knowledge gained from the observed stereodivergent and enantioselective transformations to an additional SHC-substrate pair, access to the complementary (S)-γ-dihydroionone (>99.9 % ee) could be obtained.
Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry
Parra, Andres,Lopez, Pilar E.,Garcia-Granados, Andres
experimental part, p. 421 - 439 (2010/09/05)
Starting from solid wastes from two-phase olive-oil extraction, the pentacyclic triterpenes oleanolic acid and maslinic acid were isolated. These natural compounds were transformed into methyl olean-12-en-28-oate (5), which then was transformed into several seco-C-ring triterpene compounds by chemical and photolytic modifications. The triene seco-products were fragmented through several oxidative procedures to produce, simultaneously, cis- and trans-decalin derivatives, both potential synthons for bioactive compounds. The chemical behavior of the isolated fragments was investigated, and a suitable approach to several low-molecular-weight terpenes was performed. These are interesting processes for the value-addition to solid waste from the olive-oil industry.
Ring a functionalization of terpenoids by the unusual Baeyer-Villiger rearrangement of aliphatic aldehydes
Barrero, Alejandro F.,Alvarez-Manzaneda,Alvarez-Manzaneda,Chahboun, Rachid,Mencses,Marta Aparicio
, p. 713 - 716 (2007/10/03)
A new methodology is described for transforming resinic acids into nor- alcohols and nor-olefins, via the Baeyer-Villiger rearrangement of the derived aldehyde. Based on this methodology 4-hydroxy-18-nor-abieta-8,11,13- trien-7-one and 18-nor-abieta-8,11,13-triene-4,7α-diol, two new terpenoids recently described, have been synthesized from abietic acid.
A new enantiospecific route toward monocarbocyclic terpenoids: Synthesis of (-)- caparrapi oxide
Barrero, Alejandro F.,Alvarez-Manzaneda, Enrique J.,Chahboun, Rachid,Paiz, M. Coral
, p. 9543 - 9544 (2007/10/03)
A new and efficient strategy is described for carrying out the enantiospecific synthesis of monocarbocyclic terpenoids from (-)-sclareol (1). The key steps are the Grob scission of 11-p-toluenesulphonyloxydriman- 7α-ol (2) to give the tobacco seco-sesquiterpene 3 and the Baeyer-Villiger oxidation of 4-[(1'S, 2'S)-2'-formyl-2',6',6'-trimethylcyclohexyl]-2-butanone (4), derived from 3. The first enantiospecific synthesis of (-)-caparrapi oxide (8) based on this methodology is reported.
