23665-97-6Relevant academic research and scientific papers
Total synthesis of rhodonoids a, b, e, and f, enabled by singlet oxygen ene reactions
Burchill, Laura,George, Jonathan H.
, p. 2260 - 2265 (2020)
Singlet oxygen is a versatile reagent for the selective oxidation of organic compounds under mild reaction conditions. It is frequently invoked in biosynthetic pathways, so it is especially suitable for application in the biomimetic synthesis of natural products. Herein, we show that use of the singlet oxygen ene reaction, combined with [2 + 2] cycloadditions, leads to concise, divergent, and redox-economic total syntheses of several polycyclic members of the rhodonoid family of meroterpenoids.
Efficient synthesis of biologically active (±)-confluentin and (±)-daurichromenic acid
Lee, Yong Rok,Wang, Xue,Noh, Seok Kyun,Lyoo, Won Seok
, p. 3329 - 3334 (2006)
One-step synthesis of biologically active (±)-confluentin is described from commercially available orcinol with trans,trans-farnesal in the presence of ethylenediamine diacetate as a catalyst. Further conversion of synthetic confluentin to highly potent anti-HIV agent, (±)-daurichromenic acid, is accomplished by formylation and oxidation in two steps. Copyright Taylor & Francis Group, LLC.
A Total Synthesis of (±)-Rhododaurichromanic Acid A via an Oxa-[3+3] Annulation of Resorcinols
Luo, Guo-Ying,Wu, Hao,Tang, Yu,Li, Hui,Yeom, Hyun-Suk,Yang, Ka,Hsung, Richard P.
, p. 2713 - 2720 (2015/09/15)
Development of an oxa-[3+3] annulation of vinyliminium salts with resorcinols as a 1,3-diketo equivalent is described. This annulation constitutes a cascade of Knoevenagel condensation-oxa-electrocyclization leading to a direct access to chromenes. A series of attempts was made to demonstrate its synthetic utility in natural product synthesis, culminating in a total synthesis of (±)-rhododaurichromanic acid A that also featured an intramolecular Gassman-type cationic [2+2] cycloaddition.
Efficient and general method for the synthesis of benzopyrans by ethylenediamine diacetate-catalyzed reactions of resorcinols with α,β-unsaturated aldehydes. One step synthesis of biologically active (±)-confluentin and (±)-daurichromenic acid
Lee, Yong Rok,Jung, Hyun Choi,Sang, Heum Yoon
, p. 7539 - 7543 (2007/10/03)
An efficient and general synthesis of benzopyrans is achieved by ethylenediamine diacetate-catalyzed reactions of resorcinols with α,β-unsaturated aldehydes in moderated yields. As an application of this methodology, biologically interesting confluentin, which was known to have an inhibitory effect on histamine release is synthesized in one step. Also, natural daurichromenic acid, which has highly potent anti-HIV activity, is successfully synthesized in one step.
