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Brasilamides A–D: Sesquiterpenoids from the Plant Endophytic Fungus Paraconiothyrium brasiliense
Author(s) -
Liu Ling,
Gao Hao,
Chen Xulin,
Cai Xiaoyue,
Yang Leilei,
Guo Liangdong,
Yao Xinsheng,
Che Yongsheng
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000284
Subject(s) - chemistry , circular dichroism , stereochemistry , absolute configuration , nonane
New tricyclic sesquiterpenoids brasilamides A–D ( 1 – 4 ) and the known pinthunamide ( 5 ) have been isolated from cultures of the plant endophytic fungus Paraconiothyrium brasiliense Verkley. Their structures were elucidated primarily by NMR spectroscopy, and the structure of 1 was further confirmed by X‐ray crystallography. The absolute configuration of the C‐5 tertiary alcohol in 2 was assigned by analogy to 1 and confirmed by observing the circular dichroism of in situ generated [Rh 2 (OCOCF 3 ) 4 ] complex. Compounds 2 – 4 showed modest inhibitory effects on HIV‐1 replication in C8166 cells. Compounds 1 and 2 possess an unprecedented4‐oxatricyclo‐[3.3.1.0 2,7 ]nonane skeleton.