88218-65-9Relevant academic research and scientific papers
Biomimetic Syntheses of Analogs of Hongoquercin A and B by Late-Stage Derivatization
Mies, Thomas,White, Andrew J. P.,Parsons, Philip J.,Barrett, Anthony G. M.
, p. 1802 - 1817 (2021/01/13)
The hongoquercins are tetracyclic meroterpenoid natural products with the trans-transoid decalin-dihydrobenzopyran ring system, which display a range of different bioactivities. In this study, the syntheses of a range of hongoquercins using gold-catalyzed enyne cyclization reactions and further derivatization are described. The parent enyne resorcylate precursors were synthesized biomimetically from the corresponding dioxinone keto ester via regioselective acylation, Tsuji-Trost allylic decarboxylative rearrangement, and aromatization. The dioxinone keto ester 12 was prepared in 6 steps from geraniol using allylic functionalization and alkyne synthesis.
A systematic study of functionalized oxiranes as initiating groups for cationic polycyclization reactions
Rajendar, Goreti,Corey
supporting information, p. 5837 - 5844 (2015/05/20)
Three different methods have been developed that effectively utilize chiral oxiranes derived from Katsuki-Sharpless epoxidation of allylic alcohols as initiating groups for cationic cyclization of unsaturated substrates to form chiral polycycles. This type of transformation has previously been problematic. These employ either epoxy-methoximes, vinyl-substituted oxiranes, or hydroxymethyl oxiranes. All three approaches are described in detail. In addition, this research has led to possible explanations for previously encountered difficulties in this area and provided two new insights into the Lewis acid activation of oxiranes. The methodology described herein constitutes a valuable link between two powerful synthetic constructions, enantioselective Katsuki-Sharpless epoxidation and cationic polycyclization reactions.
A simple and selective method for the O-AcCl removal using sodium borohydride
Villedieu, Emmanuelle,Lopin-Bon, Chrystel,Berteina-Raboin, Sabine
scheme or table, p. 2115 - 2118 (2010/06/14)
A deprotection of chloroacetylated alcohols using NaBH4 is reported. The free alcohols are obtained in excellent yields. The reaction was performed on primary, secondary, alkyl, allyl, benzylic alcohols and phenols. The compatibility of the method with other sensitive or protective groups is demonstrated.
Selenium dioxide E-methyl oxidation of suitably protected geranyl derivatives - Synthesis of farnesyl mimics
Fairlamb, Ian J.S.,Dickinson, Julia M.,Pegg, Mathew
, p. 2205 - 2208 (2007/10/03)
Difunctional allylic terpenes are important synthetic building blocks. Functionalisation of protected geranyl derivatives by SeO2 provides a convenient route to such compounds. The effect of the geranyl protecting group on the oxidation of the
Synthesis of (+/-)-trixagol by an electrophilic cyclization of an allylsilane
Armstrong, Rosemary J.,Weiler, Larry
, p. 2530 - 2539 (2007/10/02)
1,5-Dienes containing an allylsilane are cyclized by Lewis acids to methylenecyclohexanes.The trimethylsilyl group exerts a strong activating and directing influence on the regioselectivity of this cyclization.The monocyclic compound 10 was converted into the diterpene, (+/-)-trixagol (3).
