Convergent Total Synthesis of Ixabepilone and Its Analogues Enabled by Highly Efficient Asymmetric Hydrogenations.

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Tác giả: Gen-Qiang Chen, Ya-Nan Duan, Dong Li, Shuo Li, Haidong Xia, Renwei Xiao, Hao Yan, Xumu Zhang, Yao Zhang, Yan Zong

Ngôn ngữ: eng

Ký hiệu phân loại:

Thông tin xuất bản: Germany : Chemistry (Weinheim an der Bergstrasse, Germany) , 2025

Mô tả vật lý:

Bộ sưu tập: NCBI

ID: 736687

The convergent total synthesis of ixabepilone and its analogues in a 13-step longest linear sequence is reported. The crucial chiral centers at challenging C3-O, C8-C and C15-N positions on the scaffold of the ixabepilone were installed via highly efficient asymmetric hydrogenations (up to 95 % yield and up to 99 % e.e.) and all three fragments could be prepared on gram scale. The key aldol reaction bridges the aldehyde and keto fragments with high yield and exquisite diastereo control (8 : 1 d.r.). Finally, a novel RCM reaction conformationally controlled by a bulky silyl group was reported, which allows the facile synthesis of ixabepilone and its analogues.
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