当前位置: X-MOL 学术Org. Chem. Front. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Racemic trinorsesquiterpenoids from the Beihai sponge Spongia officinalis: structure and biomimetic total synthesis†
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2018-01-08 00:00:00 , DOI: 10.1039/c7qo01091e
Dong-Yu Sun 1, 2, 3, 4, 5 , Guan-Ying Han 5, 6, 7, 8, 9 , Na-Na Yang 1, 2, 3, 4, 5 , Le-Fu Lan 1, 2, 3, 4, 5 , Xu-Wen Li 1, 2, 3, 4, 5 , Yue-Wei Guo 1, 2, 3, 4, 5
Affiliation  

Two rare new furan butanolides, namely sponalisolides A (1) and B (2), characterized by an unprecedented furan-bearing trinorsesquiterpene alkyl chain connecting either a butanolide (1) or an N-acyl homoserine lactone moiety (2), were isolated in racemic forms from the Beihai sponge Spongia officinalis, and were further separated, by chiral-phase HPLC, to their corresponding enantiomers 1a/1b and 2a/2b, respectively. The structures, including the absolute stereochemistry, of the two pairs of enantiomeric compounds, were unambiguously established by extensive spectroscopic analysis and biomimetic total synthesis, involving a key Johnson-Claisen rearrangement and a lactone cyclization after epoxidation or dihydroxylation. All the new compounds exhibited the Pseudomonas aeruginosa quorum sensing inhibitory activity.

中文翻译:

北海海绵海绵的外消旋三正半萜类化合物:结构和仿生全合成

分离出两种罕见的新呋喃丁醇化物,即自立式固体A(1)和B(2),其特征是连接了丁醇化物(1)或N-酰基高丝氨酸内酯部分(2)的前所未有的带有呋喃基的三去倍半萜烯烷基链。来自北海海绵海绵的外消旋形式,并通过手性HPLC进一步分离为其相应的对映异构体1a / 1b2a / 2b, 分别。通过广泛的光谱分析和仿生全合成(包括关键的Johnson-Claisen重排和环氧化或二羟基化后的内酯环化),明确建立了两对对映体化合物的结构,包括绝对立体化学。所有这些新化合物均表现出铜绿假单胞菌群体感应抑制活性。
更新日期:2018-01-08
down
wechat
bug