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Total Synthesis and Structural Reassignment of Aranorosinol A, Aranorosinol B, and EI-2128-1

Haiyong Yu¹, Yingyuan Tian¹, Yan Zong¹

¹Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, 5 Yushan Road, Qingdao 266003, China.

The Journal of Organic Chemistry

|February 21, 2020

Abstract:

Herein, we report a concise and collective total synthesis of three natural products aranorosinol A, aranorosinol B, and EI-2128-1 and also the known penicimutanolone. A unified strategy was conceived, which divergently accessed all four congeners within 9-11 steps (LLS) from a common intermediate. Bisoxirane-directed 1,2-addition was utilized as a key step to generate the desired configuration of the C₈ stereocenter of aranorosinol A and B, 28 years after their first isolation, and these were both assigned as S configurations, while the C_4' and C_6' configurations of EI-2128-1 were both determined to be R,R-configurations.

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