Isolation, Structure Elucidation, and Total Synthesis of Myrtuspirone A from Myrtus communis

Cheng, Min-Jing1,2,3; Yang, Xin-Yi4; Cao, Jia-Qing3; Liu, Chao3; Zhong, Li-Ping1,2; Wang, Ying3; You, Xue-Fu4; Li, Chuang-Chuang1,2; Wang, Lei3; Ye, Wen-Cai3

2019-03-15

10.1021/acs.orglett.9b00108

ORGANIC LETTERS   影响因子和分区

1523-7060

1523-7052

A pair of enantiomeric triketone-phloroglucinol hybrids, (+)- and ()-myrtuspirone A (1), featuring an unprecedented 3-isopropyl-3H-spiro[benzofuran-2,1'-cyclohexane] backbone, were isolated from the leaves of Myrtus communis. The absolute configuration of each enantiomer of 1 was determined by X-ray diffraction and chemical calculations. Furthermore, the gram-scale total syntheses of (+/-)-1 and (-)-1 were conducted in four steps using a Michael-N-iodosuccinimide (NIS)-mediated (3 + 2)-annulation reaction. Both (+)- and (-)-I exhibited antibacterial activities against Gram-positive bacteria including multidrug-resistant strains.

SCI ; IC ; CCR

英语

NI论文

第一 ; 通讯

Shenzhen Peacock Plan[KQTD2016053117035204]

Chemistry

Chemistry, Organic

WOS:000461843900007

AMER CHEMICAL SOC

CHEMISTRY

Web of Science

1.Southern Univ Sci & Technol, Dept Chem, Shenzhen 518055, Peoples R China
2.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518055, Peoples R China
3.Jinan Univ, Guangdong Prov Key Lab Pharmacodynam Constituents, Coll Pharm, Guangzhou 510632, Guangdong, Peoples R China
4.Chinese Acad Med Sci, Beijing Key Lab Antimicrobial Agents, Lab Pharmacol, Inst Med Biotechnol,Peking Union Med Coll, Beijing 100050, Peoples R China

Cheng, Min-Jing,Yang, Xin-Yi,Cao, Jia-Qing,et al. Isolation, Structure Elucidation, and Total Synthesis of Myrtuspirone A from Myrtus communis[J]. ORGANIC LETTERS,2019,21(6):1583-1587.

Cheng, Min-Jing.,Yang, Xin-Yi.,Cao, Jia-Qing.,Liu, Chao.,Zhong, Li-Ping.,...&Ye, Wen-Cai.(2019).Isolation, Structure Elucidation, and Total Synthesis of Myrtuspirone A from Myrtus communis.ORGANIC LETTERS,21(6),1583-1587.

Cheng, Min-Jing,et al."Isolation, Structure Elucidation, and Total Synthesis of Myrtuspirone A from Myrtus communis".ORGANIC LETTERS 21.6(2019):1583-1587.