- Concise syntheses of (+)-austrodoral and (+)-austrodoric acid Based on H2O2 mediated oxidative ring contraction
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Asymmetric synthesis of the marine nor-sesquiterpenoid (+)-austrodoric acid and (+)-austrodoral in seven and nine steps respectively from Wieland-Miescher ketone was described herein. The synthesis featured an oxidative ring contraction of α-formyl cyclic ketone mediated by H2O2 to forge the hydrindane scaffold together with the contiguous quaternary carbon centers simultaneously.
- Wei, Hongbo,Zhang, Hongli,Han, Shoule,Mu, Shan,Huang, Ke,Chen, Guzhou,Xie, Weiqing
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- Divergent Synthesis of Marine Natural Products Siphonodictyal B, Corallidictyals C/D, and Liphagal Based on the Early Presence of an Aldehyde Group Instead of a Late-Stage Introduction
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An iodine-promoted sunlight-induced olefin Z/E isomerization reaction together with a palladium-catalyzed direct cross-coupling reaction of a drimanal hydrazone and an iodobenzaldehyde, without touching the aromatic aldehyde group, facilitated a divergent and expeditious access to bioactive marine natural products siphonodictyal B, corallidictyals C/D, and liphagal based on the early presence of an aldehyde group instead of a late-stage introduction.
- Wang, Jun-Li,Li, Hui-Jing,Wu, Yan-Chao
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p. 8716 - 8723
(2018/06/11)
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- Regioselective 1,2-Diol Rearrangement by Controlling the Loading of BF3·Et2O and Its Application to the Synthesis of Related Nor-Sesquiterene- and Sesquiterene-Type Marine Natural Products
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The regiocontrolled rearrangement of 1,2-diols has been achieved by controlling the loading of BF3·Et2O. Its applicability is showcased by the divergent synthesis of austrodoral, austrodoric acid, and 8-epi-11-nordriman-9-one, as well as a formal synthesis of siphonodictyal B and liphagal. A new light is shed on piancol-type rearrangements that will be useful in diversity-oriented synthesis of related natural products.
- Wang, Jun-Li,Li, Hui-Jing,Wang, Hong-Shuang,Wu, Yan-Chao
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supporting information
p. 3811 - 3814
(2017/07/26)
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- Synthetic method of austrodoral and austrodoric acid
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The invention relates to a synthetic method of an ocean terpene natural product austrodoral, austordoric acid and a land terpene natural product 8-epi-11-nordriman-9-one and belongs to the field of chemical synthesis. Sesquiterpenes vicinal diol is prepared by selective ozonization reaction of sesquiterpenes enol, the land terpene natural product 8-epi-11-nordriman-9-one and the ocean terpene natural product austrodoral are synthesized by the selective rearrangement reaction of the sesquiterpenes vicinal diol, and the ocean terpene natural product austrodoric acid is synthesized by oxidation reaction of the austrodoral. The method has the characteristics of low production cost, simple process conditions, easiness in control, suitability for industrial production, high overall yield and the like.
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Paragraph 0017; 0018
(2017/03/21)
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- Biomimetic Enantioselective Total Synthesis of (?)-Mycoleptodiscin A
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Biomimetic total synthesis of (?)-mycoleptodiscin A (1) was achieved starting from the enantiopure key intermediate, which was prepared by Friedel-Crafts reaction between 7-methoxyindole and chiral primary allylic alcohol. The crucial step in this synthes
- Dethe, Dattatraya H.,Sau, Susanta Kumar,Mahapatra, Samarpita
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p. 6392 - 6395
(2016/12/23)
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- Enantioselective access to (-)-Ambrox starting from β-farnesene
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Starting from inexpensive (E)-β-farnesene (1), an eight-step enantioselective synthesis of the olfactively precious Ambrox ((-)-2a) has been performed. The crucial step is the catalytic asymmetric isomerization of (2E,6E)-N,N-diethylfarnesylamine (3) to t
- Chapuis, Christian
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p. 197 - 214
(2014/03/21)
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- Comparative study on the larvicidal activity of drimane sesquiterpenes and nordrimane compounds against drosophila melanogaster til-til
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Natural compounds from Drimys winteri Forst and derivatives exhibited larvicidal effects against Drosophila melanogaster til-til. The most active compound was isodrimenin (4). The highest lethal concentration to the larvae of D. melanogaster was 4.5 ± 0.8 mg/L. At very low concentrations drimenol (1), confertifolin (3), and drimanol (5) displayed antifeedant and larvae growth regulatory activity. The antifeedant results of nordrimanic and drimanic compounds were better in first instar larvae. The EC50 value of polygodial (2) was 60.0 ± 4.2 mg/L; of diol 15 45.0 ± 2.8 mg/L, and of diol 17 36.9 ± 3.7 mg/L, while the new nordrimane compound 12 presented a value of 83.2 ± 3.5 mg/L.
- Montenegro, Ivan,Pino, Luis,Werner, Enrique,Madrid, Alejandro,Espinoza, Luis,Moreno, Luis,Villena, Joan,Cuellar, Mauricio
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p. 4192 - 4208
(2013/06/26)
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- Synthesis of phosphatidylinositol 3-kinase (PI3K) inhibitory analogues of the sponge meroterpenoid liphagal
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Analogues of the sponge meroterpenoid liphagal (1) have been synthesized and evaluated for inhibition of PI3Kα and PI3Kα as part of a program aimed at developing new isoform-selective PI3K inhibitors. One of the analogues, compound 24, with IC50/sub
- Pereira, Alban R.,Strangman, Wendy K.,Marion, Frederic,Feldberg, Larry,Roll, Deborah,Mallon, Robert,Hollander, Irwin,Andersen, Raymond J.
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p. 8523 - 8533
(2011/02/26)
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- Triphenylphosphine-iodine: An efficient reagent for the regioselective dehydration of tertiary alcohols
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Tertiary alcohols react under mild conditions with triphenylphosphine and iodine to give the most stable alkene in good yield.
- Alvarez-Manzaneda,Chahboun,Cabrera Torres,Alvarez,Alvarez-Manzaneda,Haidour,Ramos
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p. 4453 - 4455
(2007/10/03)
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- Enantiospecific synthesis of 8-epipuupehedione from (R)-(-)-carvone
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An enantiospecific synthesis of the antitumor marine sponge metabolite puupehedione (2a) and its C8-epimer 2b as their methylenedioxy derivatives 8a and 8b was achieved through concomitant O-allyl deprotection and electrocyclization of 20 deriv
- Maiti, Soumen,Sengupta, Sujaya,Giri, Chandana,Achari, Basudeb,Banerjee, Asish Kr.
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p. 2389 - 2391
(2007/10/03)
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- Total synthesis of a monocyclofarnesane norsesquiterpenoid isolated from mushroom ingested by beetle: Utility of solid state Baeyer-Villiger oxidation
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Norsesquiterpenoid 1 has been synthesised starting from (S)-(+)-Wieland-Miescher ketone analogue 3 via solid state Baeyer-Villiger oxidation as a key step.
- Hagiwara, Hisahiro,Nagatomo, Hidenori,Kazayama, Shin-Ichi,Sakai, Hitoshi,Hoshi, Takashi,Suzuki, Toshio,Ando, Masayoshi
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p. 457 - 459
(2007/10/03)
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- Spongiaquinone Revisited: Structural and Stereochemical Studies on Marine Sesquiterpene/Quinones from a Southern Australian Marine Sponge, Spongia sp.
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A chemical investigation of a large purple sponge, Spongia sp., from the Great Australian Bight, resulted in the isolation of a new sesquiterpene/quinone (8), together with the known compounds dehydrocyclospongiaquinone-1 (4) and spongiaquinone (2).The last compound was also isolated as the potassium salt (9), this being the first recorded account of a naturally occurring marine sesquiterpene/quinone salt.The structure for (8) was assigned by detailed spectroscopic analysis.A re-investigation into the stereostructure of spongiaquinone (2) resulted in the first unambiguous assignment of absolute stereochemistry, and uncovered the peculiar chiroptical properties of spongiaquinone (2) and its potassium salt (9).
- Capon, Robert J.,Groves, Darrin R.,Urban, Sylvia,Watson, Russell G.
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p. 1245 - 1253
(2007/10/02)
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- A NEW CHIRAL ROUTE TOWARD TERPENOIDS. ANNULATION OF CARVONE TO TRANS- AND CIS-FUSED BICYCLIC SYNTHONS
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Starting from carvone, 1 two consecutive alkylations at C-6 followed by an acid-catalyzed cyclization give new bicyclic ketones which are potentially useful chirons for synthesis of terpenes such as drimanes, labdanes and triterpenes.The stereoselectivity
- Gesson, Jean-Pierre,Jacquesy, Jean-Claude,Renoux, Brigitte
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p. 5853 - 5866
(2007/10/02)
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- Chemistry of the Podocarpaceae. LVII The Preparation of Some 1,3-Dioxans with Ambergris-Type Odours
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The preparation of a series of five-, six, seven and eight-membered ring dioxa compounds is described.All posses odours of the ambra-type, the ambergris character decreasing in intensity as the size of the dioxa ring is increased.The formation of some methoxymethyl ethers is described.
- Cambie, Richard C.,Palmer, Brian D.
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p. 1265 - 1284
(2007/10/02)
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