24190-33-8Relevant articles and documents
Chemical transformation and biological activities of ambrein, a major product of ambergris from Physeter macrocephalus (Sperm Whale)
Shen, Ya-Ching,Cheng, Shi-Yie,Kuo, Yao-Haur,Hwang, Tsong-Long,Chiang, Michael Y.,Khalil, Ashraf Taha
, p. 147 - 153 (2007)
Ten new derivatives (2-11) of ambrein (1), isolated from ambergris, were prepared by chemical transformation. Oxidation and/or cyclization were effected by reactions with selenium oxide or p-toluenesulfonyl chloride or with the use of shortwave UV light.
Dotofide, a guanidine-interrupted terpenoid from the marine slug doto pinnatifida (Gastropoda, Nudibranchia)
Putz, Annika,Kehraus, Stefan,Diaz-Agras, Guillermo,Waegele, Heike,Koenig, Gabriele M.
, p. 3733 - 3737 (2011)
An unusual natural product (dotofide, 1), in which the terpenoid skeleton is interrupted by a guanidine moiety was obtained from the marine slug Doto pinnatifida. The absolute configuration of compound 1 was deduced by ozonolysis and subsequent CD spectro
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 (1999)
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.
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.
Synthesis and olfactory evaluation of (+)- and (-)-γ-ionone
Fuganti, Claudio,Serra, Stefano,Zenoni, Alessandro
, p. 2761 - 2768 (2007/10/03)
The synthesis of enantiomerically pure (+)- and (-)-γ-ionone 3 is reported. The first step in the synthesis is the diastereoisomeric enrichment of 4-nitrobenzoate derivatives of racemic γ-ionol 12. The enantioselective lipase-mediated kinetic acetylation
Synthetic applications of the thermal rearrangement of ozonides: First enantiospecific synthesis of marine metabolite Luffarin W
Barrero,Alvarez-Manzaneda,Chahboun,Cuerva,Segovia
, p. 1269 - 1272 (2007/10/03)
The ozonides on quaternary carbons undergo thermal rearrangement to yield a mixture of formates and alkenes. This reaction constitutes an alternative procedure to the unusual Baeyer-Villiger rearrangement of aliphatic aldehydes. The first enantiospecific synthesis of the marine metabolite Luffarin W from (-)-sclareol has been carried out, based on this methodology.
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.
Synthesis and Absolute Stereochemistry of Chiral γ-Ionone and Dihydro-γ-ionone
Oritani, Takayuki,Yamashita, Kyohei
, p. 1271 - 1276 (2007/10/02)
The optical resolution of (+/-)-α-cyclogeranic acid (4) with (-)-α-methylbenzylamine gave (-)-(S)-α-cyclogeranic acid (4).Epoxidation of (-)-(S)-methyl α-cyclogeranate (5), followed by reduction with lithium aluminium hydride, gave mainly (-)-(1R,2R)-2-hydroxy-2,6,6-trimethyl-1-cyclohexanemethanol (7b), which was oxidized with pyridinium chlorochromate to give (-)-hydroxyaldehyde 8.The reaction of aldehyde 8 with 2-oxopropylidenetriphenylphosphorane gave (-)-(1'S,2'R)-2',3'-dihydro-2'-hydroxy-α-ionone (9).The thermal decomposition of (1'S)-2'-acetoxy-2',3'-dihydro-α-ionone (10) gave (-)-(S)-α-ionone (2) and (+)-(S)-γ-ionone (1).The partial hydrogenation of (+)-(S)-γ-ionone (1) gave (+)-(S)-dihydro-γ-ionone (3).
