The First Total Synthesis of 3-Oxo-11, 12, 13-trihydroxyeudesm-4-ene

The first total synthesis of 3-oxo-11, 12, 13-trihydroxyeudesm-4-ene, a highly oxygenated natural eudesmane, was described.     

13-甲氧基-6-羟基钩勿烷-5,8,11,13-四烯-7-酮的首次全合成

以α-环柠檬醛(2)为A环合成子,以间甲氧基苄基氯(3)为C环合成子,经缩合及分子内环化反应得关键中间体6.经1H NMR测试发现化合物6为全顺式结构.化合物6经氧化得双羰基化合物7.将7用t-BuOK/t-BuOH处理后得到烯醇式结构的化合物8.最后将异丙基通过Fride1-Crafts反应一步引入得到目标产物1.     

First Total Synthesis of (±)-13-Hydroxyneocembrene

First total synthesis of (±)-13-hydroxyneocembrene ( 1 ), starting from 6-methyl-5-hepten-2-one ( 6 ) and geraniol ( 7 ), is described. The key steps are (i) the addition of sulfur-stabilized carbanion 12 to aldehyde 9 , (ii) the synthesis of 18 by using phase-transfer catalyzed coupling reaction, and (iii) low-valent titanium-induced intramolecular coupling of oxo aldehyde 3 to afford the target molecule after the final deprotection.     

The First Total Synthesis of 16-Hydroxygeranylgeraniol

Facile synthesis of 16-hydroxygeranylgeranio 1,a naturally occurring alicyclic diterpene,by alkylation reaction of allylic iodide 3 with phenyl sulfone 4,is described.     

Synthesis of 6, 9, 11-Trihydroxy-6a, 12a-dehydrorotenoid

6, 9, 11-Trihydroxy-6a, 12a-dehydrorotenoid 1 (coccineone B) was synthesized from 2-hydroxybenzaldehyde 2 and phloroglucinol.     

Total Synthesis of (±)-Nimbonone and (±)-12-Ethyl-13-methoxy- 8,11,13-podocarpatriene

Most diterpenoids exhibit significant bioactivities, such as antidermatophytic, antibact- erial, and antioxidant. Although a large number of aromatic tricyclic diterpenoids have been isolated, there are a few of them having ethyl substituent. The synthesis of this type diterpenoids has been seldom reported. In order to further study the relationship between the structure and bioactivities of the diterpenoid, we extended the diterpene synthesis1,2,3. It is desirable to report herein the syn…     

3-羰基-10-去甲基-12-甲氧基-13-甲基罗汉松烷的全合成

以1,3-环己二酮为原料,经过甲基化反应和羰基保护构筑了A环合成子(5)。以邻甲基苯甲醚为原料,对位溴代、与环氧乙烷加成和进一步溴代等反应合成了C环合成子(9)。化合物5与9的格氏试剂偶联和关环反应完成目标产物3-羰基-10-去甲基-12-甲氧基-13-甲基罗汉松烷(11)的全合成。各中间体及目标产物结构均经红外光谱、核磁、质谱等表征,结果表明,成功实现了目标产物的合成。     

3-氧-11,12,13-三羟基桉烷-4-烯的简便全合成

报道了一种全合成3-氧-11,12,13-三羟基桉烷-4-烯(1)的简便方法. 对于该化合物及其衍生物的药理活性研究目前正在进行中.     

First Total Synthesis of 1,2-Dehydronephthenol

The first total synthesis of 1,2-Dehydronephthenol (15-hydroxy-cembra-1,3,7,11-tetraene), a novel cembranoid diterpene, was accomplished starting from trans, trans-farnesol through seven steps in an overall yield of 17% by employing titanium-induced intramolecular keto aldehyde reductive olefination-coupling as the key macrocyclization step.     

(±)-19-去甲基-4(18),8,11,13-四烯-松香烷-7-酮的全合成

以间异丙基溴苯1为起始原料,通过进攻环氧乙烷及溴代两步制得溴化物3.溴化物3与Hagemann′s酯发生偶联反应,水解后生成偶联产物5.再以路易斯酸BF3·Et2O催化化合物5进行分子内环化为关键步骤得到反式稠合中间体6,最后通过与三苯基膦碘甲烷季盐发生Wittig反应及氧化,合成了(±)-19-去甲基-4(18),8,11,13-四烯-松香烷-7-酮[19-nor-abieta-4(18),8,11,13-tetraen-7-one](8).     

Total Synthesis of (±)-Celaphanol A

Celaphanol A was a diterpene isolated from the stems of Celastrus stephanotifolius1, which have been the subject of continued and growing interest, due to the range of biological activities shown by many members of this family2. Some have been used in traditional medicine3 or as a stimulant4 from ancient times. In order to further study the relationship between the structure and biological activity of the diterpene compound and as an extension of diterpenoid synthesis in our laboratory5, 6, …     

3,11(13)-二烯-12-桉烷酸的立体选择性全合成

桉烷型倍半萜类化合物广泛分布于天然植物中 ,此类化合物多具有较好的生理活性 ,其中桉烷酸类化合物因具有广泛的生物活性而受到重视 .例如 ,3,1 1 ( 1 3) -二烯 - 1 2 -桉烷酸 ( 1 )呈现较好的抗菌活性[1] ,桉烷酸 ( 2 )具有消炎退热的活性[2 ] . 3,1 1 ( 1 3) -二烯 - 1 2 -桉烷酸 ( 1 )是 Shtacher等 [1] 从地中海草药Inula viscosa Ait中分离得到的 .其合成工作尚未见文献报道 .化合物 ( 1 )和 ( 2 )的结构式见 Scheme1 .Scheme1　The structures of compouds1 and2首先以烯丙基氯化为关键反应 ,在桉烷骨架的 C- 1 2位上引入一个羟基…     

First Total Synthesis of 6-Oxodendrolasinolide

~~First Total Synthesis of 6-Oxodendrolasinolide1.For a report on vinyl dithiane regioselectivity and similar reactions, see: (a) W. S. Murphy, S. Wattanasin, J. Chem. Soc, Perkin Trans. 1, 1980, 2678. (b) L. Colombo, C. Gennari, M. Santandrea, et al, J. …     

First Total Synthesis of (±)-Abieta-8, 11, 13-trien-7β-ol

The first total synthesis of (±)-abieta-8, 11, 13-trien-7β-ol (7) was accomplished via a strategy of AC→ABC, in which the reduction of the ketone 6 with LiAlH4 gave exclusively the title compound.     

Total Synthesis of Phakellistatin 13 by Solution Method

Since George R. Pettit’s group isolated cycloheptapeptide phakellistatin 1 from sponge1, over ten similar cyclic peptides have been obtained2-5. Phakellistatin 134 (Figure 1) is a cycloheptapeptide isolated from the brown snubby sponge from the South Chi…     

Synthesis of the Honey-Bee Attractant 13-Hydroxy-2-oxotridecane

13-Hydroxy-2-oxotridecane, which is isolated from extract ofEvodia hupehensisDode honey-bee eggs and actively attracts honey bees, is synthesized via ozonolysis of 1-methylcyclododecene and tetradec-13-en-2-one, the product from monoalkylation of the acetoacetic ester with 1-bromo-10-undecene followed bydecarbethoxylation, with further reduction of the intermediate peroxides using NaBH(OAc) ₃     

Synthesis of 11-hydroxydrim-8(9)-en-7-one and 11,12-dihydroxydrim-8(9)-en-7-one from drim-8(9)-en-7-one

A synthetic route to 11-hydroxydrim-8(9)-en-7-one and 11,12-hydroxydrim-8(9)-en-7-one, valuable key intermediates for the preparation of naturally occurring biologically active drimanic sesquiterpenoids, starting from easily available drim-8(9)-en-7-one was developed. 11-Hydroxydrim-8(9)-en-7-one was obtained by peracidic oxidation of the enol acetate of drim-8(9)-en-7-one. 11,12-Dihydroxydrim-8(9)-en-7-one was synthesized from drim-8(9)-en-7-one by two routes, namely, by a five-step procedurevia 11-hydroxydrim-8(9)-en-7-one and by bromination of drim-8(9)-en-7-one with NBS to give 11,12-dibromodrim-8(9)-en-7-one followed by its acetoxylation and deacetylation. Deceased Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 95–98, January, 2000.     

Synthesis of 11-hydroxydrim-8(9)-en-7-one and 11,12-dihydroxydrim-8(9)-en-7-one from drim-8(9)-en-7-one

A synthetic route to 11-hydroxydrim-8(9)-en-7-one and 11,12-hydroxydrim-8(9)-en-7-one, valuable key intermediates for the preparation of naturally occurring biologically active drimanic sesquiterpenoids, starting from easily available drim-8(9)-en-7-one was developed. 11-Hydroxydrim-8(9)-en-7-one was obtained by peracidic oxidation of the enol acetate of drim-8(9)-en-7-one. 11,12-Dihydroxydrim-8(9)-en-7-one was synthesized from drim-8(9)-en-7-one by two routes, namely, by a five-step procedurevia 11-hydroxydrim-8(9)-en-7-one and by bromination of drim-8(9)-en-7-one with NBS to give 11,12-dibromodrim-8(9)-en-7-one followed by its acetoxylation and deacetylation. Deceased Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 1, pp. 95–98, January, 2000.     

2-甲基-9-芴酮的合成

对甲苯胺与苯甲酰氯经酰胺化反应制得N-对甲苯基苯甲酰胺(1);1经傅克酰基化反应和脱酰胺保护制得2-氨基-5-甲基二苯甲酮(2);2经Pschorr环合反应合成了2-甲基-9-芴酮,总收率64%,其结构经1H NMR和HR-ESI-MS确证。     

Corylifolin 的首次全合成

类异戊二烯酚类化合物 Corylifolin(1) 是由 Snapka 等[1]于1998年从豆科植物 Psoralea Corylifolia 中分离得到的天然产物, 其结构已由波谱学和化学方法确定, 一同分离的还有化合物 Bakuchio(2). 植物 Psoralea Corylifolia 是广泛分布于中国和印度的豆科类植物, 药理实验研究表明, 此植物对 Streptococcus 和 Paramecium 等具有很高的活性, 因此它作为民间药材被长期使用. 化合物 Corylifolin(1) 和 Bakuchio(2) 具有类似的化学结构及生物活性, 是有效的DNA复制聚合酶的抑制剂, 而且具有抗肿瘤和抗诱变作用.