Shi Peng Chen

A Prophase Study on the Concise Synthesis of Aculeatin A

The 1,7-dioxadispiro [5.1.5.-pentadecane spirocyclic architecture is the main structural feature in the aculeatins which attracted scientists interesting for the remarkably high cytotoxicity, anti-bacterial and anti-protozoal activities. A prophase study on concise synthesis of the core 1,7-dioxadispiro [5.1.5.-pentadecane spirocyclic architecture of aculeatins was accomplished by using Mukaiyama aldol reaction.

Stereo-Controlled Total Synthesis of Ieodomycins A and B

A highly convergent formal synthesis of Ieodomycins A and B was achieved in 7 steps. The key features involved in the synthetic sequence of Ieodomycins A and B are the Sharpless asymmetric epoxidation and the Mukaiyama aldol reaction[. The synthesis of C-3 epimer of Ieodomycins A and B was also accomplished in good yields, but now just Heptyl diene aldehyde was getted thought 4 steps. Use Geraniol as meterials to make the corresponding aldehyde (1) via Swern oxidation. Though epoxidation, Wittig reaction and HIO4 oxidation to get the intermediate . Useing it though few steps, the target molecule can be getted.

Synthetic Study towards (±)Ieodomycin A

A concise and practical synthetic study towards racemic Ieodomycin A was described, which started from commercially available 3,7-dimethyl-2,6-octadien-1-ol (geraniol) and proceeded through a key Mukaiyama aldol reaction.

A Prophase Study on Applying Conia-Ene Reation in Constructing bicyclo [3, 3, 1] Nonane Ring

The bicyclo [3, 3, 1] nonane ring system is the main structural feature in the lycopodium alkaloids. There are many methods to build the [3, 3, 1] bridged ring system, Herein, we designed to use indium Lewis acid which can activate the triple bond to construct [3, 3, 1] bridged ring system via Conia-ene reaction, and described a prophase study of applying Conia-ene reaction to construct such bicycle [3, 3, 1] nonane ring.

Design and Synthesis of (E)-2-Hydroxy-4-Alkoxyl Salicylaldoxime Copper Extractant

Synthesis of the series of compounds, which could be put into extract copper , contained hydroformylation, etherification, oximation. Resorcinol as the starting material was transformed to 2,4-dihydroxybenzaldehyde, and then converted to 2,4-dihydroxybenzaldehyde, which oximated to (E)-2-hydroxy-4-alkoxybenzaldehyde oxime.

Study on Synthesis of 2,2-Dimethyl-3-Hydroxy-7-Octynoic Acid

Pitipeptolide A can be disconnected across the amide bind to afford t-Boc-glycine, the linear depsipeptide and the Dhoya fragment. 2,2-dimethyl-3-hydroxy-7-octynoic acid unit was prepared in eight steps from 1,5-pentanediol monobenzyl ether. including oxidation, TBS protection, deprotection and Saponification with (1M) sodium hydroxide solution gave the Dhoya unit (8) in 75% overall yield.

Synthetic Study of 1, 2, 3-Tri-O-Acetyl-5-Deoxy-D-Ribofuranose

A practical synthetic route towards 1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose from D-ribose is described, which started from D-ribose and proceeded through ketalization,esterification,reduction,hydrolysis and acetylation in more than 30% overall yield.

Study on Synthesis of 2-(1-Tert-Butoxycarbonylamino-2-Methyl-Butyl)-Thiazole-4-Carboxylic Acid Methyl Ester

2-(1-tert-Butoxycarbonylamino-2-methyl-butyl)-thiazole-4-carboxylic acid methyl ester, the chiral unit containing thiazole of a novel cyclic depsipeptide Lyngbyabellin A which exhibited moderate cytotoxicity against KB and LoVo cells, was synthesized from N-t-Boc-L-isoleucine and L-serrine methyl ester monohydrochloride in overall yield 15% through six steps, including condensation, TBS protection, thionation, deprotection, cyclodehydration and aromatization. The ee value of the title chiral thiazole unit is up to 98％.

Study on Synthesis of (S)-Methyl 2-(2, 2, 5, 5-Tetramethyl-1, 3-Dioxolan-4-Yl)Thiazole-4-Carboxylic Acid Methyl Ester

(S)-methyl 2-(2, 2, 5, 5-tetramethyl-1, 3-dioxolan-4-yl) thiazole-4-carboxylic acid methyl ester, the unit containing thiazole of a cyclic depsipeptide Lyngbyabellin A which exhibited moderate cytotoxicity against KB and LoVo cells, was synthesized from methyl 3, 3-dimethylacrylate in overall yield 13.8% through nine steps, including asymmetric dihydroxylation, 2, 2-dimethoxypropane protection, saponification, coupling reaction, sulphonation, diazotization, cyclization, oxidation, and so on.

Study on Synthesis of (R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynylox-azolidine

(R)-2,2-Dimethyl-3-(tert-butoxycarbonyl)-4-ethynylox-azolidine, an intermediate of the natural product jaspine B, which was isolated from various sponges and endowed with cytotoxic activity against several human carcinoma cell lines, was synthesized from L-Serine in overall yield 43% through seven steps, including esterification, Boc protection, acetonization, reduction, Swern oxidation and Corey-Fuchs reaction.