期刊
ORGANIC LETTERS
卷 23, 期 11, 页码 4203-4208出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01139
关键词
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资金
- National Natural Science Foundation of China [81803545, 81973438]
- NSFC-Joint Foundation of Yunnan Province [U1902213]
- Fok Ying-Tong Education Foundation [161039]
- Guangdong Province Key Area R&D Program of China [2020B1111110003]
- Three-Year Development Plan Project for Traditional Chinese Medicine [ZY(2018-2020)-CCCX-2001-02]
- A Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning
The asymmetric total synthesis of five biologically significant polycyclic polyprenylated acylphloroglucinols (PPAPs), including garcinol and cambogin, was achieved through a highly diastereoselective and stereodivergent strategy. An efficient cascade Dieckmann cyclization was employed to construct the bicyclo[3.3.1]nonane core in one step. The synthesis provided a general approach toward the chiral endo-type B PPAPs and their C-30 diastereomers in a single sequence, which resolved the challenges of the absolute configuration determination/structural revision of PPAPs bearing exocyclic stereocenters.
The asymmetric total synthesis of five biologically significant polycyclic polyprenylated acylphloroglucinols (PPAPs), including garcinol and cambogin, was achieved through a highly diastereoselective and stereodivergent strategy. Along the way, an efficient cascade Dieckmann cyclization was employed to construct the bicyclo[3.3.1]nonane core in one step. The synthesis provided a general approach toward the chiral endo-type B PPAPs and their C-30 diastereomers in a single sequence, which resolved the challenges of the absolute configuration determination/structural revision of PPAPs bearing exocyclic stereocenters.
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