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Total synthesis, structural revision and biological evaluation of γ-elemene-type sesquiterpenes

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Abstract

Total synthesis and absolute configuration confirmation of γ-elemene-type sesquiterpenes, which possess vast potential for biological activities, was investigated based on a convergent synthetic strategy. A key intermediate with all functional groups of this family of natural products was accessed by an intermolecular aldol reaction and then an acetylation of a known ketone (12) derived from commercially available verbenone. The versatile intermediate can be easily transformed into structurally different γ-elemene-type sesquiterpenes based on control of base-promoted cyclization manipulation in different solvents. The utility of this robust approach is illustrated by the first syntheses of elema-1,3,7(11),8-tetraen-8,12-lactam (4′) and 8β-methoxy-isogermafurenolide (6a), as well as the syntheses of elem-1,3,7,8-tetraen-8,12-olide (3) and hydroxyisogermafurenolide (5) in only 6 or 7 steps. In addition, the structure of the reported 5βH-elem-1,3,7,8-tetraen-8,12-olide (1) was revised as elem-1,3,7,8-tetraen-8,12-olide (3) by comparison of their identified datum, and the absolute configuration of elema-1,3,7(11),8-tetraen-8,12-lactam was confirmed as 4′. Furthermore, the inhibitory effect of all synthesized natural compounds and their natural analogues on cancer cell proliferation was evaluated. Among them compounds 3, 4 and 4′ were found to possess potent inhibitory activity against Kasumi-1 and Pfeiffer. Meanwhile, preliminary structure–activity relationships for these compounds are discussed.

Graphical abstract: Total synthesis, structural revision and biological evaluation of γ-elemene-type sesquiterpenes

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Publication details

The article was received on 16 Aug 2018, accepted on 02 Oct 2018 and first published on 03 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02005A
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Total synthesis, structural revision and biological evaluation of γ-elemene-type sesquiterpenes

    C. Yuan, S. Zhong, X. Li, Y. Wang, M. Xun, Y. Bai and K. Zhu, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB02005A

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