Total synthesis of cis-solamin and its inhibitory action with bovine heart mitochondrial complex I

A convergent total synthesis of cis-solamin (1a) and its diastereomer (1b) was accomplished. A key reaction of this approach was the use of VO(acac)₂-catalyzed diastereoselective epoxidation of (Z)-bis-homoallylic alcohol 3 followed by spontaneous cyclization for the cis-THF ring formation. By comparison of the optical rotation of the two possible diastereomers, it is suggested that the absolute configuration of natural cis-solamin is 1a. Inhibitory action of synthetic 1a and 1b with bovine heart mitochondrial complex I are reported.     

An iterative acetylene-epoxide coupling strategy for the total synthesis of longimicin C

Longimicin C, a naturally occurring annonaceous acetogenin possessing a C₂-symmetrical bis-THF moiety and a short hydrocarbon chain between its THF-containing region and a terminal γ-lactone, was synthesized for the first time. The total synthesis was successfully achieved by an iterative acetylene-epoxide coupling strategy. d-Mannitol was used to establish the bis-THF-containing segment, in which the additional stereochemistries were introduced by Sharpless dihydroxylations and intramolecular Williamson etherifications. Regioselective epoxide-openings by the appropriate terminal acetylenes allowed coupling and elaboration of all four fragments including the introduction of three essential hydroxyls into the proper sites of the target skeleton.     

Synthesis of a Mimicking Hybrid of Annonaceous Acetogenin with Steroid for Antitumoral Activity Investigation

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Two-directional synthesis of the non-adjacent bis(tetrahydrofuran) core of cis-sylvaticin

Synthesis of the C₂-symmetric, non-adjacent bis(tetrahydrofuran) core of cis-sylvaticin in seven steps and 24% overall yield from (2R,3S)-1,2-epoxy-4-penten-3-ol is reported. A strategy involving assembly of the central 1,4-diol unit by silicon-tethered ring-closing metathesis and subsequent two-directional functionalization, including establishment of the cis/threo stereochemical relationships of the tetrahydrofuran rings by Sharpless asymmetric dihydroxylation/S_N2 cyclization, is employed.     

番荔枝内酯————明日抗癌之星

本文介绍一类近年来被发现于番荔枝科(Annonaceae)植物中的强抗肿瘤活性化合物----番荔枝内酯(annonaceousacetogenin) , 从这类化合物的结构特点, 生理活性, 生源假说, 化学合成等几个方面综述了在该领域的氧基状况 .     

天然番荔枝内酯类化合物构效关系研究进展

番荔枝内酯类化合物化学结构及抗肿瘤作用机制独特.综述了这类天然化合物的构效关系研究进展.     

Synthesis ofLepidoptera pheromones using acetylenes

Syntheses of acetogenin pheromones using acetylene derivatives are reviewed.Institute of Petroleum Chemistry and Catalysis, Academy of Sciences of the Republic of Bashkortostan and Ufa Scientific Center, Russian Academy of Sciences, 450075, Ufa, pr. Oktyabrya, 141. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 12–31, January–February, 2000.     

Atemoyacin A: A new bis-tetrahydrofuranyl annonaceous acetogenin from Annona atemoya H.

Atemoyacin A, a new annonaceous acetogenin was isolated from the alcoholic extract of the seeds of Annona atemoya Hort (Annonaceae). Its structure and relative configuration were elucidated on the basis of the spectral analysis.     

阿蒂莫耶番荔枝内酯的研究

本文首次报道从阿蒂莫耶番荔枝(Annona atemoya Hort)种子中分离到七个白色蜡状固体, 经光谱鉴定, 它们分别为已知的抗肿瘤活性番荔枝内酯(annonaceous acetogenin)-Asimicin, Motrilin, Isodesacetyluvaricin,Cherimolin-1, Almunequin, Squamocin-K和Neoannonin。     

双四氢呋喃环番荔枝内酯类似物以及annonacin与钙离子配位行为研究

作为结构活性关系研究的一部分，利用NMR配位羟基积分法、配位滴定法以及 紫外平衡移动分光光度法，研究了化合物1～5和钙离子的配位行为，发现羟基所在 碳的绝对构型对配位有明显的影响。