- Annulation-retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products
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A new and highly efficient annulation-retro-Claisen cascade, which involves the [4 + 1] or [5 + 1] annulation of α-benzoylacetates with bielectrophilic peroxides and a subsequent debenzoylation process under mild basic conditions, has been developed for the rapid construction of valuable tetrahydrofuran- and dihydropyran-2-carboxylates in good yields. By employing the new reaction, the unified total synthesis of γ- and δ-lactone natural products such as (±)-tanikolide, (±)-goniothalamins, (±)-7-epi-goniodiol, and (±)-plakolide A has been accomplished in 4-7 steps.
- Hu, Lin,Li, Jialin,Li, Xuemin,Xu, Qianlan
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supporting information
p. 274 - 277
(2022/01/03)
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- Design, synthesis, in vitro cytotoxicity evaluation and structure-activity relationship of Goniothalamin analogs
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A series of six/five member (E/Z)-Goniothalamin analogs were synthesized from commercially available (3,4-dihydro-2H-pyran-2-yl)methanol/5- (hydroxymethyl)dihydrofuran-2(3H)-one in three steps with good to moderate overall yields and their cytotoxicity against lymphoblastic leukemic T cell line (Jurkat E6.1) have been evaluated. Among the synthesized analogs, (Z)-Goniothalamin appeared to be the most active in cytotoxicity (IC 50 = 12 μM). Structure-activity relationship study indicates that introducing substituent in phenyl ring or replacing phenyl ring by pyridine/naphthalene, or decreasing the ring size of lactones (from six to five member) do not increase the cytotoxicity.
- Mohideen, Mazlin,Zulkepli, Suraya,Nik-Salleh, Nik-Salmah,Zulkefeli, Mohd,Weber, Jean-Frédéric Faizal Abdullah,Rahman, A. F. M. Motiur
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p. 812 - 831
(2013/07/26)
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- Gold-catalyzed intermolecular reactions of propiolic acids with alkenes: [4 + 2] Annulation and enyne cross metathesis
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A gold-catalyzed intermolecular reaction of propiolic acids with alkenes led to a [4 + 2] annulation or enyne cross metathesis. The [4 + 2] annulation proceeds with net cis-addition with respect to alkenes and provides an expedient route to α,β-unsaturate
- Yeom, Hyun-Suk,Koo, Jaeyoung,Park, Hyun-Sub,Wang, Yi,Liang, Yong,Yu, Zhi-Xiang,Shin, Seunghoon
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supporting information; experimental part
p. 208 - 211
(2012/02/16)
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