Concise formal synthesis of (+)-pyripyropene A

A concise enantioselective synthesis of A/B bicyclic segment of naturally occurring α-pyrone meroterpenoid pyripyropene A is achieved in 9 steps (LLS) and 7.5% yield starting from R-(−)-carvone. The significant points of the synthesis include: (1) an intramolecular 1, 3-dipolar cycloaddition reactio...

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Bibliographic Details
Published in:Tetrahedron 2019-07, Vol.75 (29), p.3939-3942
Main Authors: Li, Tao, Wu, Guangmiao, Feng, Shangbiao, Hu, Xiaojun, Zhang, Weiwei, Tang, Shouchu, Xie, Xingang, She, Xuegong
Format: Article
Language:English
Subjects:
(+)-Pyripyropene A
(R)-(−)-Carvone
[3+2]-Cycloaddition
Formal synthesis
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Summary:A concise enantioselective synthesis of A/B bicyclic segment of naturally occurring α-pyrone meroterpenoid pyripyropene A is achieved in 9 steps (LLS) and 7.5% yield starting from R-(−)-carvone. The significant points of the synthesis include: (1) an intramolecular 1, 3-dipolar cycloaddition reaction to construct the A ring and assemble C4 quaternary carbon stereocenter as well; (2) reductive cleavage of the oxazole motif utilized Raney Ni/B(OCH3)3. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2019.06.017