Stereoselective Synthesis of trans-Decalin-Based Spirocarbocycles via Photocyclization of 1,2-Diketones

Sijia Chen; Zhongchao Zhang; Chongguo Jiang; Chunbo Zhao; Haojie Luo; Jun Huang; Zhen Yang

doi:10.1021/acsomega.1c02054

Stereoselective Synthesis of trans-Decalin-Based Spirocarbocycles via Photocyclization of 1,2-Diketones

ACS Omega. 2021 Jul 13;6(29):18848-18859. doi: 10.1021/acsomega.1c02054. eCollection 2021 Jul 27.

Authors

Sijia Chen¹, Zhongchao Zhang¹, Chongguo Jiang¹, Chunbo Zhao¹, Haojie Luo¹, Jun Huang¹, Zhen Yang^{1

2

3}

Affiliations

¹ State Key Laboratory of Chemical Oncogenomics and Key Laboratory of Chemical Genomics, Peking University Shenzhen Graduate School, Shenzhen 518055, China.
² Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), and Peking-Tsinghua Center for Life Sciences, Peking University, Beijing 100871, China.
³ Shenzhen Bay Laboratory, Shenzhen 518055, China.

Abstract

Diastereoselective synthesis of the trans-decalin-based α-hydroxyl butanone spirocarbocycles bearing all-carbon quaternary stereogenic centers has been achieved via Norrish-Yang photocyclization of trans-decalin-substituted-2,3-butanediones using daylight. Density functional theory (DFT) calculations suggest that this diastereoselective reaction is affected by both substrate conformation and intramolecular hydrogen bonds. The developed chemistry could be applied to synthesizing the derivatives of the trans-decalin-based biologically important natural products.