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Biomimetic Cationic Cyclization toward ent-Kaurene-type Diterpenoids 被引量:1
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作者 Lili Zhu Ran Hong 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2013年第1期111-118,共8页
Terpenoids comprise the largest family of natural products and include various structurally different genus which play important roles in living organisms. Biosynthetically, diterpenoids are derived from (E,E,E)-ger... Terpenoids comprise the largest family of natural products and include various structurally different genus which play important roles in living organisms. Biosynthetically, diterpenoids are derived from (E,E,E)-geranylgeranyl diphosphate (GGPP). From GGPP, diterpene cyclase catalyzes a sequence of carbocation- mediated cyclizations, rearrangements, and further oxidations, leading to a class of structurally unique ent-kaurenes, such as cafestol, gibberellin A3 and oridonin. According to the biosynthesis pathway of ent-kaurene, we designed a chiral acetal-enabled and SnCln-promoted biomimetic polyene cationic cyclization. With a following Birch reduc- tiort/alkylation cascade, a core skeleton of representative ent-kaurenes diterpenoids was completed. 展开更多
关键词 DITERPENOID ent-kaurene biomimetic synthesis carbocation cyclization Birch reduction/alkylationcascade
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ent-Kaurene全碳骨架中AB环系的不对称合成
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作者 马文静 朱礼志 +1 位作者 章梦珣 李志成 《有机化学》 SCIE CAS CSCD 北大核心 2022年第2期580-589,共10页
本课题组前期利用多样性导向合成策略完成ent-kaurene天然产物Xerophilusin I、Neolaxiflorin L、Eriocalyxin B、15-epi-Enmelol全合成工作,为完成该类天然产物的不对称合成,对Horner-Wadsworth-Emmons反应进行了优化,改善了反应的区... 本课题组前期利用多样性导向合成策略完成ent-kaurene天然产物Xerophilusin I、Neolaxiflorin L、Eriocalyxin B、15-epi-Enmelol全合成工作,为完成该类天然产物的不对称合成,对Horner-Wadsworth-Emmons反应进行了优化,改善了反应的区域选择性,在酸性条件下后处理,将Z/E混合物转化为单一Z构型.基于温和的酸性条件实现了单一构型的转化,提出了氢键辅助的Michael加成/retro-Michael消除的机理猜想.发展了Cu(OTf)_(2)催化的不对称Diels-Alder反应:以烯醇硅醚的双烯体3、β-酮酸酯1为亲双烯体,在噁唑啉为手性配体的条件下,以65%的收率和>19∶1dr值完成AB环的构建. 展开更多
关键词 ent-kaurene天然产物 Horner-Wadsworth-Emmons反应 区域选择性 不对称DIELS-ALDER反应
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A New 1β-hydroxy-ent-kaurenoid From Isodon Enanderianus 被引量:1
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作者 Yan Hong WANG Yao Zu CHEN +1 位作者 Zhong Wen LIN Han Dong SUN (School of Chemistry and Chemical Engineering, Zhongshan University, Guangzhou 510275)(State Key Laboratory of Applied organic Chemistry, Lanzhou University, Lanzhou, 730000, and Department of Chemi 《Chinese Chemical Letters》 SCIE CAS CSCD 1998年第8期733-734,共2页
A new 1β-hydroxy-ent-kauren diterpenoid, enanderianin C1, has been isolated from the leaves of Isodon enanderianus, and its structure has been elucidated by spectroscopic evidences.
关键词 LABIATAE isodon enanderianus ent-kauren DITERPENE
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Two New Diterpenoids from Isodon rubescens 被引量:1
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作者 Bao Lin LI Shao Nong CHEN +2 位作者 Zhi Xian SHI Xuan TIAN Yao Zu CHEN 《Chinese Chemical Letters》 SCIE CAS CSCD 2000年第1期43-44,共2页
Two new diterpenoids taibairubescensin A (1) and B (2) have been isolated from Isodon rubescens. The structures of compound 1 and 2 were elucidated as 2 beta,3 beta-diacetoxy-11 beta,13 alpha-dihydroxy-ent-kaur- 16-en... Two new diterpenoids taibairubescensin A (1) and B (2) have been isolated from Isodon rubescens. The structures of compound 1 and 2 were elucidated as 2 beta,3 beta-diacetoxy-11 beta,13 alpha-dihydroxy-ent-kaur- 16-en-15-one (1) and 3 beta,11 beta-diacetoxy-2 beta,6 alpha-dihydroxy-ent-kaur-16-en-15-one (2) on the basis of spectroscopic analysis. 展开更多
关键词 Isodon rubescens taibairubescensin A taibairubescensin B ent-kaurene diterpenoids
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