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Amin PM, Su Z, Wang S. Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A. J Org Chem. 2021;86(21):15318-15325doi: 10.1021/acs.joc.1c01890.
Amin, P. M., Su, Z., & Wang, S. (2021). Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A. The Journal of organic chemistry, 86(21), 15318-15325. https://doi.org/10.1021/acs.joc.1c01890
Amin, Pathan Mosim, et al. "Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A." The Journal of organic chemistry vol. 86,21 (2021): 15318-15325. doi: https://doi.org/10.1021/acs.joc.1c01890
Amin PM, Su Z, Wang S. Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A. J Org Chem. 2021 Nov 05;86(21):15318-15325. doi: 10.1021/acs.joc.1c01890. Epub 2021 Oct 15. PMID: 34652914.
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J Org Chem. 2021 Nov 05;86(21):15318-15325. doi: 10.1021/acs.joc.1c01890. Epub 2021 Oct 15.

Gold-Catalyzed Cycloisomerization of Propargyl Pyruvates Enabling Unified Access to Tricladolides C and D, Chaetomellic Anhydride A, and Tyromycin A.

The Journal of organic chemistry

Pathan Mosim Amin, Zhenjie Su, Shaozhong Wang

Affiliations

  1. State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.

PMID: 34652914 DOI: 10.1021/acs.joc.1c01890

Abstract

Gold-catalyzed cycloisomerization of propargyl pyruvates has been developed as a key reaction to prepare maleic anhydride-type natural products. By combining with chemoselective epoxidation of the formed γ-alkylidenebutenolides and oxidative cleavage of epoxides, the first synthesis of tricladolide D and racemic tricladolide C has been achieved in 52 and 16% overall yields with five to seven steps starting from commercially available compounds. Further catalytic hydrogenation of alkenylated maleic anhydrides derived from γ-alkylidenebutenolides produced chaetomellic anhydride A (19% yield for six steps) and tyromycin A (15% yield for six steps), which provides flexible synthetic approaches to these naturally occurring dialkylated maleic anhydrides distinct from the documented ones.

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