1216-84-8Relevant articles and documents
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.
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.
Cambie et al.
, p. 1767,1775 (1972)
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
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Stoll,Hinder
, p. 1984,1897 (1953)
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Ruzicka,Seidel,Engel
, p. 621,623 (1942)
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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.
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.
Chiral complementary alkyl heterocyclic compounds and their use as fungicides
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Paragraph 0060-0064, (2020/10/20)
The invention relates to a chiral drimane heterocyclic compound and a purpose of the chiral drimane heterocyclic compound as a sterilizing agent. A chemical structural general formula of the compoundis shown as a formula (I), in the formula (I), 8-bit stereo configuration is R or S, and represents the heterocyclic compound, comprising iso-oxazoline, isoxazole, pyrazoline, pyrimidine, benzimidazole and pyrimidine, or diazepine.
Flavin Nitroalkane Oxidase Mimics Compatibility with NOx/TEMPO Catalysis: Aerobic Oxidization of Alcohols, Diols, and Ethers
Thapa, Pawan,Hazoor, Shan,Chouhan, Bikash,Vuong, Thanh Thuy,Foss, Frank W.
, p. 9096 - 9105 (2020/08/14)
Biomimetic flavin organocatalysts oxidize nitromethane to formaldehyde and NOx - providing a relatively nontoxic, noncaustic, and inexpensive source for catalytic NO2 for aerobic TEMPO oxidations of alcohols, diols, and ethers. Alcohols were oxidized to aldehydes or ketones, cyclic ethers to esters, and terminal diols to lactones. In situ trapping of NOx and formaldehyde suggest an oxidative Nef process reminiscent of flavoprotein nitroalkane oxidase reactivity, which is achieved by relatively stable 1,10-bridged flavins. The metal-free flavin/NOx/TEMPO catalytic cycles are uniquely compatible, especially compared to other Nef and NOx-generating processes, and reveal selectivity over flavin-catalyzed sulfoxide formation. Aliphatic ethers were oxidized by this method, as demonstrated by the conversion of (-)-ambroxide to (+)-sclareolide.
