Synthesis of Spirotricyclic Core of Bonnadiene

Lin, Xiaohong1; Huang, Yu1; Min, Long1; Li, Chuang-Chuang1,2

2023-02-01

10.1021/acs.orglett.3c00142

ORGANIC LETTERS   Impact Factor & Quartile

1523-7060

1523-7052

We herein describe a new approach for the efficient synthesis of the tricyclic core of diterpene bonnadiene. The synthetically challenging and unusual [6-7-5] spirotricyclic skeleton including the all-carbon quaternary stereocenter, was installed diastereoselectively via a type II [5 + 2] cycloaddition, followed by a unique vinylogous semipinacol rearrangement. The described chemistry demonstrates the feasibility of making the [6-7-5] spirotricyclic skeleton of the final product from the strained bridged [7-8-5] ring system.

SCI

English

NI Journal Papers

First ; Corresponding

National Natural Science Foundation of China["22271137","22225102"] ; National Key R&D Program of China[2022 YFE 0 2 0 5 5 0 0] ; Shenzhen Bay Laboratory[SZBL2021080601005] ; Research Projects of Universities of Guangdong Province["2021KCXTD024","2019KZDXM005"] ; Shenzhen Science and Technology Innovation Committee[JCYJ20210324104408023]

Chemistry

Chemistry, Organic

WOS:000937454200001

AMER CHEMICAL SOC

CHEMISTRY

2-s2.0-85148041120

Web of Science

1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Guangdong Prov Key Lab Catalyt Chem, Shenzhen 518055, Peoples R China
2.Shenzhen Bay Lab, Shenzhen 518132, Peoples R China

Lin, Xiaohong,Huang, Yu,Min, Long,et al. Synthesis of Spirotricyclic Core of Bonnadiene[J]. ORGANIC LETTERS,2023,25(7):1156-1160.

Lin, Xiaohong,Huang, Yu,Min, Long,&Li, Chuang-Chuang.(2023).Synthesis of Spirotricyclic Core of Bonnadiene.ORGANIC LETTERS,25(7),1156-1160.

Lin, Xiaohong,et al."Synthesis of Spirotricyclic Core of Bonnadiene".ORGANIC LETTERS 25.7(2023):1156-1160.