202339-11-5Relevant articles and documents
Synthesis of isotopically labelled oligoprenyl diphosphates and their application in mechanistic investigations of terpene cyclases
Citron, Christian A.,Rabe, Patrick,Barra, Lena,Nakano, Chiaki,Hoshino, Tsutomu,Dickschat, Jeroen S.
, p. 7684 - 7691 (2015/04/22)
A flexible, efficient and robust method for the synthesis of isotopically labelled oligoprenyl diphosphates was developed. The method makes use of just a few building blocks (acetone, triethyl phosphonoacetate, and ethyl acetoacetate) from which several i
Total synthesis of cristatic acid based on late-stage decarboxylative allylic migration and biomimetic aromatization of a diketo dioxinone
George, Nicolas S.,Anderson, Katie E.,Barrett, Anthony G. M.
, p. 7604 - 7610 (2013/12/04)
A fifteen-step synthesis of methyl cristatate is described. tert-Butyl-[(E)-6-iodo-3-methylhex-2-enyloxy)]diphenylsilane, synthesized from geraniol, was coupled with 2-(diethoxymethyl)-4-lithiofuran and transformed - by acetal hydrolysis, Wittig olefinati
Biomimetic cyclization of epoxide precursors of indole mono-, sesquiand diterpene alkaloids by lewis acids
Isaka, Tetsuya,Hasegawa, Morifumi,Toshima, Hiroaki
experimental part, p. 2213 - 2222 (2012/02/14)
Cyclization of the synthesized epoxide precursors of indole mono-, sesqui- and diterpene alkaloids was performed to elucidate the mechanism for biomimetic cationic cyclization to polycyclic structures. 3-(6,7- Epoxygeranyl)indole (11), 3-(10,11-epoxyfarne
Development of a concise and diversity-oriented approach for the synthesis of plecomacrolides via the diene-ene RCM
Lu, Kui,Huang, Mengwei,Xiang, Zheng,Liu, Yongxiang,Chen, Jiahua,Yang, Zhen
, p. 1193 - 1196 (2007/10/03)
A concise synthesis of the core structures of plecomacrolide with ring sizes varying from 16 to 19 atoms was achieved for the first time by the diene-ene ring-closing olefin metathesis reaction. This approach should allow access to the structurally divers
Stereoselective disposition of the geminal dimethyl group in the cyclization of geranyl acetate under zeolite confinement conditions
Tsangarakis, Constantinos,Stratakis, Manolis
, p. 4435 - 4439 (2007/10/03)
The stereochemistry in the acid-catalysed biomimetic cyclization of [8,8,8-D3]geranyl acetate was examined in solution and under conditions of zeolite Y confinement. In the intrazeolite reaction the gem-allylic methyl group adopts a diastereose
Pheromone synthesis, CXCVI. Synthesis of germacrene-B and its extension to the synthesis of (±)-9-methylgermacrene-B, the racemate of the male- produced sex pheromone of the sandfly Lutzomyia longipalpis from Lapinha, Brazil
Muto, Shin-Etsu,Nishimura, Yutaka,Mori, Kenji
, p. 2159 - 2165 (2007/10/03)
Both germacrene-B (2) and 9-methylgermacrene-B [(±)-1] were synthesized by employing cyclization reactions [8 → 9 and (±)-20 → (±)-21] as the key steps. The latter [(±)-1] was shown to be the racemate of the male-produced sex pheromone of the sandfly Lutz
Advanced Tetracycles in a Stereoselective Approach to d,l-Spongiatriol and Related Metabolites: The Use of Radicals in the Synthesis of Angular Electrophores
Zoretic, Phillip A.,Zhang, Yongzheng,Fang, Haiquan,Ribeiro, Anthony A.,Dubay, George
, p. 1162 - 1167 (2007/10/03)
A stereoselective radical cascade cyclization of polyene 6, containing an α,β-unsaturated cyano group, was employed to control six contiguous chiral centers and to introduce a C-8 angular CN group in tricycle 7. The cyano group was ultimately utilized as an entry to a C-8 angular hydroxymethyl group. Compound 7 was converted into two key tetracycles 22 and 25, respectively, each possessing an intact D-furan ring system and containing the necessary functionality for further chemical elaboration to the highly oxygenated spongians 1-5.
