20764-21-0Relevant academic research and scientific papers
Asymmetric induction with cyclodextrins: Photocyclization of tropolone alkyl ethers
Koodanjeri, Smriti,Joy, Abraham,Ramamurthy
, p. 7003 - 7009 (2000)
Employing the photobehavior of tropolone alkyl ethers as the probe, we have established that cyclodextrins could as a serve as medium to bring about enantioselective photoreactions. The enantioselectivity observed in this study is moderate at best. The enantioselectivity observed in the solid state in comparison to aqueous solution suggests that a rigid environment may be essential to achieve chiral induction during photoreactions of organic molecules. In this context the much higher enantioselectivity observed for the same systems within zeolites is noteworthy. (C) 2000 Elsevier Science Ltd.
CHIROPTICAL STUDIES OF LABILE OR DIFFICULT TO RESOLVE MOLECULES GENERATED BY CHIRAL LASER PHOTOCHEMISTRY.1. (1S,5R)-1-METHOXYBICYCLOHEPTA-3,6-DIEN-2-ONE
Cavazza, Marino,Zandomeneghi, Maurizio,Festa, Crescenzo,Lupi, Enrico,Sammuri, Manuela,Pietra, Francesco
, p. 1387 - 1390 (1982)
The optical activity of (1S,5R)-1-methoxybicyclohepta-3,6-dien-2-one (1) is determined by partial photoresolution of the racemate with circularly polarized laser light; although a rearranged, optically active product was also formed, isolation of the 1 enantiomers was not required.
Synthesis and biological evaluation of (±)-hippolachnin and analogs
Winter, Nils,Rupcic, Zeljka,Stadler, Marc,Trauner, Dirk
, p. 375 - 383 (2019/04/26)
Due its unique structure and its reported potent antifungal activity, the marine polyketide hippolachnin A (1) has attracted much attention in the synthetic community. Herein, we describe the development of a concise, diversifiable and scalable synthesis of the racemic natural product, which serves as a platform for the generation of bioactive analogues. Biological testing of our synthetic material did not confirm the reported antifungal activity of hippolachnin A but unraveled moderate activity against nematodes and microbes.
Thiocarbonyl Ylide Chemistry Enables a Concise Synthesis of (±)-Hippolachnin A
Winter, Nils,Trauner, Dirk
, p. 11706 - 11709 (2017/09/08)
Hippolachnin A (1) is an antifungal polyketide that bristles with ethyl groups mounted onto a caged heterotricyclic core. It has shown potent activity against Cryptococcus neoformans, a yeast that can affect immunocompromised patients as an opportunistic pathogen. Herein we describe a concise, diversifiable, and scalable synthesis of (±)-hippolachnin A (1). It features a powerful photochemical opening step, a diastereoselective addition of an ethyl cuprate and an unusual strategy to install two additional ethyl groups that makes use of a thiocarbonyl ylide generated in situ.
The Total Synthesis of Prostaglandins by the Tropolone Route
Greene, Andrew E.,Teixeira, Marco A.,Barreiro, Eliezer,Cruz, Alicia,Crabbe, Pierre
, p. 2553 - 2564 (2007/10/02)
A general synthesis from α-tropolone methyl ether of natural and modified prostaglandins is detailed.A key intermediate in the synthesis, 7-methoxybicyclohepta-3,6-dien-2-one, has been secured from α-tropolone methyl ether in improved yield and con
Synthetic Photochemistry. XIII. Chiroptical Retention for the Reported "antara-antara"-3,3-Sigmatropy of Bicyclohepta-3,6-dien-2-ones
Takeshita, Hitoshi,Kumamoto, Masatoshi,Kuono, Isao
, p. 1006 - 1009 (2007/10/02)
Troponoids were shown to form 2:1-complexes with β-cyclodextrin and 1:1 complexes with α-cyclodextrin.The photoisomerization of complexed tropolone and 2-methoxytropone gave optically active 1-hydroxy- and 1-methoxybicyclohepta-3.6-dien-2-ones in improved yields.The pyrolysis of the (+)-1-methoxybicyclohepta-3,6-dien-2-one gave the (+)-3-methoxybicyclohepta-3,6-dien-2-one, ruling out the two-fold supra-antara-1,3-sigmatropy.
