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Preparation method of Icetaxane type abietane diterpene

A technology of abietane diterpene and methylation, which is applied in the field of drug synthesis and can solve problems such as poor chemoselectivity

Active Publication Date: 2021-04-27
CENT SOUTH UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned method has poor chemoselectivity, and what is obtained is a mixture

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  • Preparation method of Icetaxane type abietane diterpene

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Embodiment Construction

[0046] The conception and technical effects of the present invention will be clearly and completely described below in conjunction with the embodiments, so as to fully understand the purpose, features and effects of the present invention. Apparently, the described embodiments are only some of the embodiments of the present invention, rather than all of them. Based on the embodiments of the present invention, other embodiments obtained by those skilled in the art without creative efforts belong to The protection scope of the present invention.

[0047] The chemical reagents used in the following steps were all commercially available starting materials without further processing. The reaction yield of each step is calculated as the separation yield of column chromatography. The reaction of each step is detected by Qingdao silica gel thin layer analysis plate under UV, and the ethanol solution of sulfuric acid and phosphomolybdic acid is infiltrated and heated to develop color. ...

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Abstract

The invention discloses a preparation method of Icetexane type abietane diterpene, which comprises the following steps: S1, adding carnosic acid into a methylation system, carrying out solid-liquid separation, and collecting a solid phase to obtain an intermediate 2; s2, adding the intermediate 2 into a reduction system, carrying out solid-liquid separation, and collecting a solid phase to obtain a prepared intermediate 3; and S3, adding the intermediate 3 into a rearrangement system, carrying out solid-liquid separation, and collecting a solid phase to obtain the Icetaxane diterpene. The synthesis method disclosed by the invention has the characteristics of short reaction time, high selectivity, high yield, large-scale preparation and no protection of key steps, and can be widely popularized and applied.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular to a preparation method of an Icetexane type abietane diterpene. Background technique [0002] Icetexane-type abietane diterpenoids are B-ring-expanded abietane diterpenoids. There are more than 70 natural products of this type that have been reported so far. They are widely distributed and found in many families of plants. (-)-Barbatusol was first isolated from Coleus barbatus Bentham as an Icetexane-type abietane diterpene, and animal experiments showed that it has strong antihypertensive activity. (-)-Barbatusol (CAS 88515-76-8) is also present in Salvia przewalskii. [0003] (-)-Barbatusol has a low content in plants and is mainly prepared by synthetic methods. The total synthesis of icetexane-type abietane diterpenes is based on a metal-mediated cycloisomerization strategy. In the related art, the intramolecular Friedel-Crafts reaction (Friedel-Crafts) cyclization of ...

Claims

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Application Information

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IPC IPC(8): C07C37/00C07C39/17C07C67/08C07C69/757
CPCC07C37/002C07C37/00C07C67/08C07C2603/26C07C2603/32C07C69/757C07C39/17
Inventor 邓旭周应军曹伟刘婷婷杨舒婷曾光尧
Owner CENT SOUTH UNIV
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