Brasilamides A–D: Sesquiterpenoids from the Plant Endophytic Fungus  Paraconiothyrium brasiliense | Zendy

Liu Ling | Zendy; Gao Hao | Zendy; Chen Xulin | Zendy; Cai Xiaoyue | Zendy; Yang Leilei | Zendy; Guo Liangdong | Zendy; Yao Xinsheng | Zendy; Che Yongsheng | Zendy

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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.

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