20404-65-3Relevant academic research and scientific papers
Concise syntheses of (+)-austrodoral and (+)-austrodoric acid Based on H2O2 mediated oxidative ring contraction
Wei, Hongbo,Zhang, Hongli,Han, Shoule,Mu, Shan,Huang, Ke,Chen, Guzhou,Xie, Weiqing
, (2019)
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.
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
Wang, Jun-Li,Li, Hui-Jing,Wu, Yan-Chao
, p. 8716 - 8723 (2018/06/11)
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.
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
Wang, Jun-Li,Li, Hui-Jing,Wang, Hong-Shuang,Wu, Yan-Chao
, p. 3811 - 3814 (2017/07/26)
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.
Synthetic method of austrodoral and austrodoric acid
-
Paragraph 0017; 0018, (2017/03/21)
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.
Biomimetic Enantioselective Total Synthesis of (?)-Mycoleptodiscin A
Dethe, Dattatraya H.,Sau, Susanta Kumar,Mahapatra, Samarpita
supporting information, p. 6392 - 6395 (2016/12/23)
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
Enantioselective access to (-)-Ambrox starting from β-farnesene
Chapuis, Christian
, p. 197 - 214 (2014/03/21)
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
Comparative study on the larvicidal activity of drimane sesquiterpenes and nordrimane compounds against drosophila melanogaster til-til
Montenegro, Ivan,Pino, Luis,Werner, Enrique,Madrid, Alejandro,Espinoza, Luis,Moreno, Luis,Villena, Joan,Cuellar, Mauricio
, p. 4192 - 4208 (2013/06/26)
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.
Synthesis of phosphatidylinositol 3-kinase (PI3K) inhibitory analogues of the sponge meroterpenoid liphagal
Pereira, Alban R.,Strangman, Wendy K.,Marion, Frederic,Feldberg, Larry,Roll, Deborah,Mallon, Robert,Hollander, Irwin,Andersen, Raymond J.
supporting information; scheme or table, p. 8523 - 8533 (2011/02/26)
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
Triphenylphosphine-iodine: An efficient reagent for the regioselective dehydration of tertiary alcohols
Alvarez-Manzaneda,Chahboun,Cabrera Torres,Alvarez,Alvarez-Manzaneda,Haidour,Ramos
, p. 4453 - 4455 (2007/10/03)
Tertiary alcohols react under mild conditions with triphenylphosphine and iodine to give the most stable alkene in good yield.
Enantiospecific synthesis of 8-epipuupehedione from (R)-(-)-carvone
Maiti, Soumen,Sengupta, Sujaya,Giri, Chandana,Achari, Basudeb,Banerjee, Asish Kr.
, p. 2389 - 2391 (2007/10/03)
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
