Lignan natural product as well as intermediate and preparation method thereof

Abstract

The invention provides a lignan natural product as well as an intermediate and a preparation method thereof. The intermediate is a chiral tetrahydrofuran ring compound V or X containing three three-dimensional centers. The preparation method comprises the following steps: by taking a palladium complex generated by coordination of a palladium source and a chiral ligand as a catalyst, reacting 4-vinyl-1,3-dioxolan-2-one with a compound IV in a solvent under the action of the catalyst to obtain the chiral tetrahydrofuran ring compound V or X containing three three-dimensional centers. According to the preparation method of the lignan natural product, a chiral tetrahydrofuran ring compound V or X is adopted as a reactant for preparation, and then reduction, olefin oxidation, intramolecular cyclization and the like are conducted to finally obtain the lignan natural product with optical purity, so that compared with an existing asymmetric total synthesis method, the method is shortened in reaction steps, and has the advantages that the reaction raw materials are convenient and easy to obtain, the operation is simple, the reaction conditions are mild, and the yield, diastereoselectivity and enantioselectivity of the reaction product are high.

Description

technical field [0001] The invention relates to the field of chemical industry, in particular to a lignan natural product and its intermediate, a preparation method of the lignan natural product, and a preparation method of an intermediate of the lignan natural product. Background technique [0002] The natural product lignans have numerous structures due to their different substituents and different configurations of linkage modes, and widely exist in various plants. In the past few decades, 100 lignans have been isolated from various plants. A variety of lignan natural products. In addition, various biological activities of such natural products have been reported, including antitumor, antioxidant, antihypertensive, antidiabetic, anti-inflammatory and antiviral activities, etc. However, so far there are relatively few reports on asymmetric total synthesis methods for such natural products. Most of the only methods rely on chiral pools or chiral auxiliary agents to complet...

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Problems solved by technology

However, so far there are relatively few reports on asymmetric total synthesis methods for such natural products. Most of the only methods rely on chiral pools or chiral auxiliary agents to complete through longer synthetic steps. Recently, Kan and Hamashima et al. reported the asymmetric synthesis of some lignan natural products via asymmetric aldol condensation reaction as the key step through 9 reaction steps

In fact, although the research on various biological activities has been quite mature so far, many lignan natural products have not been related to biological research, and there are few reports on their mode of action and structure-activity structure-activity relationship.

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