Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, ...Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.展开更多
The asymmetric total synthesis of herbarumin Ⅲ 3, a naturally occurred phytotoxin, along with 8-epi-herbantmin Ⅲ 22, was succeeded in 12 steps from n-butyraldehyde based on Brown＇s asymmetric allylation, taking mod...The asymmetric total synthesis of herbarumin Ⅲ 3, a naturally occurred phytotoxin, along with 8-epi-herbantmin Ⅲ 22, was succeeded in 12 steps from n-butyraldehyde based on Brown＇s asymmetric allylation, taking modified Julia olefination and Yamaguchi＇s macro-lactonization as key steps.展开更多
An efficient route to the natural products bupleurynol and its analog（RB-2）,isolated from Bupleuri Radix,was established based on versatile intermediate（15）.In this synthetic route,Sonogashira and CadiotChodkiewic...An efficient route to the natural products bupleurynol and its analog（RB-2）,isolated from Bupleuri Radix,was established based on versatile intermediate（15）.In this synthetic route,Sonogashira and CadiotChodkiewicz coupling as well as Julia-Kocienski olefination are utilized as key steps.The highly efficient synthetic route provides opportunities to explore the biological behavior of bupleurynol and RB-2.展开更多
基金Project supported by the National Natural Science Foundation of Chinathe State Key Laboratory of Bio-organicNatural Products Chemistry
文摘Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.
基金The project was supported by the National Natural Science Foundation of China(No.20672050).
文摘The asymmetric total synthesis of herbarumin Ⅲ 3, a naturally occurred phytotoxin, along with 8-epi-herbantmin Ⅲ 22, was succeeded in 12 steps from n-butyraldehyde based on Brown＇s asymmetric allylation, taking modified Julia olefination and Yamaguchi＇s macro-lactonization as key steps.
基金financially supported by National Natural Science Foundation of China(Nos.21402111,81473415)Basic research program of Shanxi Province(No.2015021039)+1 种基金Shanxi Scholarship Council of China(No.2015-020)science and technology innovation project of Shanxi Province(No.2016115)
文摘An efficient route to the natural products bupleurynol and its analog（RB-2）,isolated from Bupleuri Radix,was established based on versatile intermediate（15）.In this synthetic route,Sonogashira and CadiotChodkiewicz coupling as well as Julia-Kocienski olefination are utilized as key steps.The highly efficient synthetic route provides opportunities to explore the biological behavior of bupleurynol and RB-2.
