José Manuel Botubol Ares

• Bachelor of Chemistry
• Universidad de Cádiz

Premyrsinane-type diterpenoids have been considered to originate from the cyclization of a suitable 5,6- or 6,17-epoxylathyrane precursor. Their biological activities have not been sufficiently explored to date, so the development of synthetic or microbial approaches for the preparation of new derivatives would be desirable. Epoxyboetirane A (4) is...

Lathyrane-type diterpenes have a wide range of biological activities. Among them, euphoboetirane A (1) exerts neurogenesis-promoting activity. In order to increase the structural diversity of this type of lathyrane and explore its potential use in neurodegenerative disorders, the biotransformation of 1 by Streptomyces puniceus BC-5GB.11 has been in...

Lathyrane-type diterpenes have a wide range of biological activities. Among them, euphoboetirane A (1) exerts neurogenesis-promoting activity. In order to increase the structural diversity of this type of lathyranes to explore their potential use in neurodegenerative disorders, the biotransformation of 1 by Streptomyces puniceus BC-5GB.11 has been...

An efficient ruthenium-catalyzed N-alkylation of amines, amides and sulfonamides has been developed employing novel pentamethylcyclopentadienylruthenium (II) complexes bearing the methylene linked bis(NHC) ligand bis(3-methylimidazol-2-ylidene)methane. The acetonitrile complex 2 has proven particularly effective with a broad range of substrates wit...

The complex [Cp*RuCl(COD)] reacts with LH2Cl2 (L = bis(3-methylimidazol-2-ylidene)) and LiBun in tetrahydrofuran at 65 °C furnishing the bis—(carbene) derivative [Cp*RuCl(L)] (2). This compound reacts with NaBPh4 in MeOH under dinitrogen to yield the labile dinitrogen-bridged complex [{Cp*Ru(L)}2(μ-N2)][BPh4]2 (4). The dinitrogen ligand in 4 is rea...

This short review aims to provide an overview of the use of Cp2Ti(III)Cl and other related titanocene(III) species as coordinating reagents­ in template reactions in the selective preparation of C–C and C–O bonds. These complexes are able to assemble two components to produce powerful reactions possessing high regio-, chemo-, diastereo-, and enanti...

A novel diterpenoid, gaditanone (2), which possesses an unprecedented 5/6/4/6-fused gaditanane tetracyclic ring skeleton, and a new jatrophane (1) were isolated from the aerial parts of Euphorbia gaditana. The chemical structures and absolute configurations were determined by extensive spectroscopic NMR studies and ECD data analysis. A proposed bio...

A novel methodology for the epoxidation of a broad range of primary, secondary, and tertiary allylic alcohols is described using tert-butyl hydroperoxide as oxidant and Ti(III) species generated by reduction of Ti(IV) complexes, with manganese (0) in 1,4-dioxane under mild reaction conditions. The reaction proceeded with wide substrate scope and hi...

Two new macrocyclic diterpenes, 2-epi-latazienone (4) and 15β-acetoxy-7β-nicotinoyloxy-3β8α-di-(2-methylpropanoyloxy)-4αH,9αH,11αH-lathyra-5E,12E-dien-14-one (5), and three known lathyrane-type diterpenes (1-3) were isolated from Euphorbia laurifolia latex. Their structures were determined on the basis of a detailed analysis of their 1D and 2D NMR...

A method has been developed for the conversion of primary, secondary, and tertiary alcohols, and phenol, into the corresponding esters at room temperature. The method uses a titanium(III) species generated from a substoichiometric amount of titanocene dichloride together with manganese(0) as a reductant, as well as methylene diiodide. It involves a...

Supporting Information

The reaction of geraniol with different lithium carbenoids generated from n-BuLi and the corresponding dihaloalkane has been evaluated. The reaction occurs in a chemo and stereoselective manner, which is consistent with a directing effect from the oxygen of the allylic moiety. Furthermore, a set of polyenes containing allylic hydroxyl or ether grou...

A method for the conversion of primary, secondary and tertiary alcohols into the corresponding THF ethers at room temperature and primary and secondary alcohols into the corresponding THP ethers, has been developed using titanium(III) species generated from a catalytic amount of titanocene dichloride or (4R,5R)-(–)-2,2-dimethyl-α,α,α′,α′-tetra(1-na...

Covering: 1963 up to the end of 2014The biological activities of aristolane, aromadendrane, ent-1,10-secoaromadendrane, 2,3-secoaromadendrane, ent-5,10-cycloaromadendrane, bicyclogermacrene, lepidozane, and maaliane terpenoids which contain the gem-dimethylcyclopropyl unit are described. Particular attention is given to their anti-viral, anti-micro...

A new method for the chemo- and stereoselective conversion of allylic alcohols into the corresponding cyclopropane derivatives has been developed. The cyclopropanation reaction was carried out with an unprecedented titanium carbenoid generated in situ from Nugent's reagent, manganese and methylene diiodide. The reaction involving the participation...

The synthesis of several derivatives of 3-hydroxy-2,4,8-trimethyldec-8-enolide and attempts at the synthesis of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (), a structure which has been assigned to a metabolite of the phytopathogenic fungus, Botrytis cinerea, gave products whose spectroscopic data had significant differences from those reported...

The structure, 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1), was assigned to a metabolite of Botrytis cinerea but the spectra of several synthetic analogues had significant differences from that of 1. Examination of the constituents of a B. cinerea mutant that overproduces polyketides, gave sufficient quantities of 1, now named cinbotolide, f...

The enantioselective synthesis of (2R,3R,4E,8E)-3-hydroxy-2,4,8-trimethyldeca-4,8-dienolide () by ring-closing metathesis is described. This compound is an analogue of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide () which is a rare 11-membered lactone produced by the fungus, Botrytis cinerea. Mutasynthetic studies with compound using two mutants...

Covering: 1973 to 2013 The biological activities of tigliane, lathyrane, ingenane, casbane, jatropholane and premyrsinane diterpenoids which contain the gem-dimethylcyclopropyl unit are described. Particular attention is given to their anti-viral, anti-microbial and cytotoxic activities. In the main text there are 132 references. The electronic sup...

Chemical genetics is an emerging field that can be used to study the interactions of chemical compounds, including natural products, with proteins. Usually, the identification of molecular targets is the starting point for studying a drug’s mechanism of action and this has been a crucial step in understanding many biological processes. While a grea...

The asymmetric synthesis of the antibacterial and antitu-moral natural compound xylariolide A (1) and five stereoiso-mers has been achieved. The strategy is based on the one-pot epoxidation/lactonisation or dihydroxylation/lactonisa-tion of the hypothetical biosynthetic intermediate xylarioicA acid (8). The absolute configuration of xylariolide A w...

The asymmetric synthesis of key fragments of the phytotoxic toxins botcinolide/botcinin is reported. The synthesis of 1 and 1a are based on a convergent route via esterification and alkene metathesis of fragments A, B or C, B, which were obtained by Evans aldol condensation and stereoselective crotylation, respectively.