Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 29, Pages 9211-9218Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b05070
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Funding
- National Natural Science Foundation of China [21525209, 21621002, 21772225, 21761142003]
- Chinese Academy of Sciences (Strategic Priority Research Program) [XDB20000000]
- Chinese Academy of Sciences (Key Research Program of Frontier Sciences) [QYZDB-SSW-SLH040]
- Shanghai Science and Technology Commission [15JC1400400, 17XD1404600]
- National Program for Support of Top Notch Young Professionals of China
- K. C. Wong Education Foundation
- Syngenta
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Aplysiasecosterol A (1) is a structurally unusual 9,11-secosteroid isolated from the sea hare Aplysia kurodai. We have accomplished the first and asymmetric total synthesis of 1 in a convergent fashion. The left-hand segment bearing three adjacent stereocenters was constructed through desymmetrizing reduction, ketalization, and radical cyclization. A strategy of asymmetric 2-bromoallylation followed by spontaneous desymmetrizing lactolization enabled a more expeditious access to this segment. The right-hand segment was prepared through two different approaches: one featuring Myers alkylation and Suzuki-Miyaura coupling and the other relying upon Aggarwal lithiation-borylation and Zweifel-Evans olefination. The two fragments were coupled by a Reformatsky type reaction. The three consecutive stereocenters embedded in the central domain of 1 were generated by an iron-mediated, hydrogen atom transfer based radical cyclization reaction.
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