1216-84-8Relevant academic research and scientific papers
Microbial transformation of sesquiterpenes, (-)-Ambrox and (+)-sclareolide
Choudhary, M. Iqbal,Musharraf, Syed Ghulam,Sami, Amtul,Atta-Ur-Rahman
, p. 2685 - 2694 (2004)
The microbial transformation of (-)-Ambrox (1), a perfumery sesquiterpene, by a number of fungi, by means of standard two-stage-fermentation technique, afforded ambrox-1α-ol (2), ambrox-1α,11α-diol (3), ambrox-1α,6α-diol (4), ambrox-1α,6α,11α-triol (5), ambrox-3-one (6), ambrox-3β-ol (7), ambrox-3β,6β-diol (8), 13,14,15,16-tetranorlabdane-3,8,12-triol (9), and sclareolide (10) (Schemes 1 and 2). Further incubation of compound 10 with Cunninghamella elegans afforded 3-oxosclareolide (11), 3β-hydroxysclareolide (12), 2α- hydroxysclareolide (13), 2α,3β-dihydroxysclareolide (14), 1α,3β-dihydroxysclareolide (15), and 3β-hydroxy-8-episclareolide (16) (Scheme 3). Metabolites 2-5, 12, 13, and 16 were found to be new compounds. The major transformations include a reaction path involving hydroxylation, ether-bond cleavage and inversion of configuration. Metabolites 11-16 of sclareolide showed significant phytotoxicity (Table I). The structures of the metabolites were characterized on the basis of spectroscopic techniques.
TOTAL SYNTHESIS OF (+/-)-APLYSIN-20
Murai, Akio,Abiko, Atsushi,Masamune, Tadashi
, p. 4955 - 4958 (1984)
The first total synthesis of (+/-)-aplysin-20 involving 16 steps from nerolidol in a 10percent overall yield is described.
SYNTHESIS OF (+/-)-NORAMBREINOLIDE BY CYCLIZATION OF TRANS-β-MONOCYCLOHOMOFARNESIC ACID
Saito, Akira,Matsushita, Hajime,Tsujino, Yasuko,Kaneko, Hajime
, p. 757 - 760 (1981)
Synthesis of norambreinolide by acid-catalized cyclization of trans-β-monocyclohomofarnesic aicd was studied.From the acid norambreinolide was obtained in 57 per cent by catalysis of stannic chloride in dichloromethane at -78 deg C.Isomerization of norambreinolide to norisoambreinolide was observed with a rise of reaction temperature in the presence of stannic chloride.
Synthesis and antifungal activity of ethers, alcohols, and iodohydrin derivatives of sclareol against phytopathogenic fungi in vitro
Ma, Miaofeng,Feng, Jili,Li, Ruoxin,Chen, Shu-Wei,Xu, Hui
, p. 2773 - 2777 (2015)
This study synthesized 20 sclareol derivatives. The antifungal activities of these derivatives were evaluated in vitro against five phytopathogenic fungi using the mycelium growth rate method. Among all the tested compounds, compound 16 with one iodine atom and three hydroxyl groups displayed higher fungicidal activities against all the tested phytopathogenic fungi than precursor sclareol. Compound 16 also showed more pronounced antifungal activities against Curvularia lunata (IC50 = 12.09 μg/mL) and Alternaria brassicae (IC50 = 14.47 μg/mL) than the positive control, a commercial agricultural fungicide thiabendazole.
Efficient enantioselective synthesis of (+)-sclareolide and (+)-tetrahydroactinidiolide: chiral LBA-induced biomimetic cyclization
Upar, Kiran B.,Mishra, Sanjay J.,Nalawade, Shrikant P.,Singh, Soni A.,Khandare, Reena P.,Bhat, Sujata V.
, p. 1637 - 1640 (2009)
An efficient enantioselective synthesis of the lactones (+)-sclareolide and (+)-tetrahydroactinidiolide has been achieved through Lewis acid-assisted chiral Bronsted acid-induced enantioselective cyclization of terpenic carboxylic acids. The reaction sequ
FUNCTIONALIZATION AT C-12 IN LABDANIC DITERPENES: SYNTHESIS OF THE NATURAL DITERPENIC LACTONES ISOLATED FROM CISTUS LADANIFERUS L.
Teresa, J. de Pascual,Urones, J. G.,Pedrero, A. Montanna,Barcala, P. Basabe
, p. 5717 - 5720 (1985)
Oxidative cyclization of Labdanediol (XII) and methyl Labdanolate (Ib) with Pb(OAc)4, and subsequent oxidation with reagents as RuO4, O3, CrO3 or (tBu)2CrO4 affords, in excellent yield, the natural diterpenic lactones II, III, VII, VIII, XI and XIII, isolated from Cistus ladaniferus L.
Synthesis of alkenes from tertiary esters utilizing the triphenylphosphine-iodine system
Alvarez-Manzaneda,Chahboun,Cabrera Torres,Alvarez,Alvarez-Manzaneda,Haidour,Ramos
, p. 1075 - 1077 (2005)
The treatment of tertiary esters with triphenylphosphine and iodine under mild conditions gives the most stable alkene in good yield. Formates, acetates and trifluoroacetates were studied.
SUPERACID CYCLIZATION OF HOMO- AND BISHOMOISOPRENOID ACIDS
Vlad, P. F.,Ungur, N. D.,Perutskii, V. B.
, p. 246 - 249 (1991)
The superacid cyclization of a number of homo- and bishomoterpenoid acids, the products of which are γ- and δ-lactones - important natural compounds or intermediates for the synthesis and manufacture of valuable substances - was investigated.It is shown that the superacid cyclization of homo- and bishomoterpenoid acids to γ- and δ-lactones proceeds stereospecifically, chemoselectively, and structurally selectively, is general in character, and ensures high yields of the desired products.
A practical synthesis of ambrox from sclareol using no metallic oxidant
Moulines,Lamidey,Desvergnes-Breuil
, p. 749 - 758 (2001)
The commercial synthesis of Ambrox is modified so that the key intermediate, the sclareolide, results from an indirect Oxidative degradation of sclareol. This method allows to greatly alleviate the waste disposal problem and to raise the overall yield of Ambrox to 75%.
Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds
Doiuchi, Daiki,Uchida, Tatsuya
supporting information, p. 7301 - 7305 (2021/10/01)
We found that the oxygen atom of water is activated to iodosylbenzene derivatives via reversible hydrolysis of PhI(OOCR)2 and can be used to the oxygen source for ruthenium(bpga)-catalyzed site-selective C-H oxygenation. Ru(bpga)/PhI(OOCR)2/H2O system, sterically less bulky methinic and methylenic C-H bonds in various compounds can be converted to desired oxygen functional groups in a site-selective manner. Using this method, oxygen-isotope labeled compounds such as d-[3-17O/18O]-mannose can be prepared in a multigram scale.
