38419-75-9Relevant academic research and scientific papers
Transformations of sclareol oxide by bromination. Synthesis of driman-8α, 11-diol from sclareol oxide
Aricu,Andreeva,Vlad
, p. 2644 - 2648 (1996)
Depending on reaction conditions, the reaction of sclareol oxide with N-bromosuccinimide affords either 12-bromo-or 12,16-dibromosclareol oxide, whereas the reaction of sclareol oxide with bromine in methanol gives 12-monobromide or (13S)-11,12-dibromo-8α
Synthesis of acuminolide and 17-O-acetylacuminolide from (+)-sclareolide
Zoretic, Phillip A.,Fang, Haiquan,Ribeiro, Anthony A.,Dubay, George
, p. 1156 - 1161 (1998)
The synthesis of natural acuminolide and 17-O-acetylacuminolide is reported. Commercially available (+)-sclareolide was converted to epoxy alcohol 3, which upon acid-catalyzed cyclization afforded tricycle 14. Reaction of 14 with 1O2 in the presence of a hindered base gave an inseparable mixture of acuminolide 1a and 16-epiacuminolide 1b in a 70:30 ratio. Chromatographic separation of the diacetates of 1a and 1b afforded pure 18a and 18b. An analogous reaction sequence was used in the synthesis of 17-O-acetylacuminolide (2a) and 16-epi-17-O-acetylacuminolide (2b).
Practical synthesis of Ambrox from farnesyl acetate involving lipase catalyzed resolution
Tanimoto, Hisahide,Oritani, Takayuki
, p. 1695 - 1704 (1996)
Enantiomerically pure Ambrox was synthesized from (-)-13,14,15,16- tetranor-8α,12-labdanediol, which was prepared by lipase catalyzed kinetic resolution of (±)-drimane-8,11-diol.
Enantioselective synthesis of 11-homodrim-7-en-9α,12,13-triol
Vlad,Edu,Koltsa,Chokyrlan,Nikolescu,Delyanu
, p. 574 - 578 (2011)
The enantioselective synthesis of 11-homodrim-7-en-9α,12,13-triol, a convenient synthon for preparing polyfunctional 11-homodrimane sesquiterpenoids, was carried out starting from norambreinolide, a cleavage product available from several bicyclic labdane diterpenoids.
An Efficient Synthesis of Wiedendiol-A from (+)-Sclareolide
Chackalamannil, Samuel,Wang, Yuguang,Xia, Yan,Czarniecki, Michael
, p. 5315 - 5318 (1995)
An efficient synthesis of Wiedendiol-A (1) is described starting from commercially available (+)-sclareolide.This synthesis also confirms the absolute stereochemistry of Wiedendiol-A.
212. Significance of the Geminal Dimethyl Group in the Odor Principle of Ambrox
Ohloff, Guenther,Giersch, Wolfgang,Pickenhagen, Wilhelm,Furrer, Anton,Frei, Beatrice
, p. 2022 - 2029 (1985)
The diastereoisomeric 18-nor- and 19-norambrox ((6α)- and (6β)-dodecahydro-3a,6,9a-trimethylnaphtholfurans resp.) as well as the corresponding 18,19-dinor-derivatives (dodecahydro-3a,9a-dimethylnaphthofurans) have been synthesized and subjected to sensory evaluation.Threshold data and odor determination give an enlarged insight into the structure-activity relationship (SAR) in ambrox-type ambergris fragrances.As a general conclusion, the accumulation of axial CH3 groups in the tricyclic ethers 1-12 leads to the strongest receptor affinity.
Synthesis of Ambrox from (-)-sclareol and (+)-cis-abienol
Barrero, Alejandro F.,Alvarez-Manzaneda, Enrique J.,Altarejos, Joaquin,Salido, Sofia,Ramos, Jose M.
, p. 10405 - 10412 (1993)
Short and efficient syntheses of (-)-Ambrox (12) from (-)-sclareol (1) and (+)-cis-abienol (11) are described.In contrast to previously described procedures, the transformation of 1 to 12, involving in the key step, an oxidative degradation by catalytic osmium tetroxide, in the presence of sodium periodate, has the advantage of using the more suitable sodium borohydride, as the reducing agent.The isolation and characterization of some reaction intermediates allowed us to confirm the degradation mechanism.
Total synthesis of (-)-thallusin: Utilization of enzymatic hydrolysis resolution
Yamamoto, Hirofumi,Takagi, Yuichi,Oshiro, Takaki,Mitsuyama, Tadashi,Sasaki, Ikuo,Yamasaki, Naoto,Yamada, Akiyo,Kenmoku, Hiromichi,Matsuo, Yoshihide,Kasai, Yusuke,Imagawa, Hiroshi
, p. 8850 - 8855 (2014)
Thallusin, isolated from a marine bacterium, is the only known natural product to act as an algal morphogenesis inducer. Because (-)-thallusin can only be obtained in exceedingly limited amounts from microbial cultivation, a synthetic supply of this compound is highly desirable. Here, we describe a novel synthetic pathway to (±)-thallusin and the first asymmetric synthesis of (-)-thallusin utilizing the enzymatic hydrolysis resolution with the combination of lipase PS-30 and lipase M Amamo-10.
A study on the synthesis of antiangiogenic (+)-coronarin A and congeners from (+)-sclareolide
Oh, Sangtae,Jeong, In Howa,Shin, Woon-Seob,Lee, Seokjoon
, p. 2009 - 2012 (2003)
Coronarin A 1, epi-coronarin A 2 and some synthetic intermediates 14a and 14b synthesized from sclareolide exhibit good growth inhibition activities on HUVEC proliferation. In particular, coronarin A 1 and epi-coronarin A 2 effectively suppressed the growth factor induced tube formation of HUVEC at the concentration of 10 μg/mL.
The synthesis of (-)-Ambrox starting from labdanolic acid
Bolster, Marjon G,Jansen, Ben J.M,De Groot, Aede
, p. 5657 - 5662 (2001)
Iododecarboxylation of labdanolic acid (1), followed by dehydrohalogenation led to alkenes 4 and 12. Both compounds were converted into (1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyldecahydro-2- naphthalenol (8), which was transformed via cyclization into (-)-Ambrox (9).
