Method for stereoselective synthesis of IeodomycinA and B

A technology of stereoselectivity and synthesis method, applied in chemical instruments and methods, asymmetric synthesis, organic chemistry methods, etc., can solve the problems of long synthesis steps and achieve the effect of high synthesis cost

Inactive Publication Date: 2014-04-30
JIANGXI SCI & TECH NORMAL UNIV
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Problems solved by technology

[0003] The methods for the synthesis of compounds Leodomycin A and B reported in the current litera

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  • Method for stereoselective synthesis of IeodomycinA and B
  • Method for stereoselective synthesis of IeodomycinA and B

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[0029] In order to make the present invention clearer, the following further describes the present invention in detail with reference to embodiments. It should be understood that the specific embodiments described here are only used to explain the present invention, but not to limit the present invention.

[0030] 1. Synthesis of compound 2

[0031] Dissolve oxalyl chloride (9 mL, 97.24 mmol) in dry dichloromethane (120 mL) at -78°C, then dissolve dimethyl sulfoxide (14 mL, 194.49 mmol) in dichloromethane ( 50 mL), and mix again. After 15 minutes, slowly add geraniol (10.0 g, 64.83 mmol) to the mixed solution within 30 minutes. Dissolve triethylamine (66 mL, 374.72 mmol) in dry dichloromethane (80 mL), slowly add this mixture to the reaction flask, and then continue to keep it at -78℃ for 1 h, and then The reaction flask was placed in ice water until room temperature, overnight. After spotting the plate to detect the reaction, the reaction was quenched with hydrochloric acid solu...

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Abstract

The invention relates to a method for asymmetric synthesis of chain nonsaturated ester IeodomycinA and B. The method utilizes geraniol as a raw material and through Swern oxidation, 3-chloroperbenzoic acid epoxidation reaction, Wittig reaction and periodic acid oxidation cutting-off reaction, an intermediate 5 is prepared. Through a two-step reaction with trimethylchlorosilane, methyl acetoacetate as an intermediate 2 is prepared. Silyl enol ether 8 and aldehyde 5 are synthesized into a key intermediate 9 in the presence of a titanium tetraisopropanolate/(S)-BINOL as a catalyst. Through hydroxyl-induced reduction reactions, the end product IeodomycinA and B are synthesized. The method comprises the eight steps, has a simple and reasonable design, utilizes cheap raw materials and has a high product yield. The IeodomycinA and B have high optical purity.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a novel method for the asymmetric synthesis of a class of natural antibacterial and antitumor compounds Leodomycin A. and B. technical background [0002] The natural products Leodomycin A and B (see figure 1 ) is a secondary metabolite of marine fungi with anticancer and antibacterial activities isolated for the first time by Shin et al. The biological activity test found that the compound has high inhibitory effect on Bacillus subtilis and Escherichia coli, and has high cytotoxicity on human cancer cells. Due to its good biological activity, it has attracted great interest from synthetic chemists, biologists and pharmacologists. [0003] The current methods for synthesizing compounds Leodomycin A and B reported in the literature have problems such as long synthesis steps, or need to use a large amount of expensive chiral auxiliaries. Contents of the invention ...

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Application Information

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IPC IPC(8): C07C69/732C07C67/31C07D309/30C07B53/00
CPCC07B53/00C07C67/31C07C67/343C07D301/00C07D303/04C07D309/30C07C69/732C07C69/738
Inventor 黄双平张建廷竹承林王李平王晓季
Owner JIANGXI SCI & TECH NORMAL UNIV
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