[²H₂₆]-1-epi-Cubenol, a completely deuterated natural product from Streptomyces griseus

• Christian A. Citron and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 2841–2845, doi:10.3762/bjoc.9.319

• ; terpenes; Introduction The actinomycete Streptomyces griseus is a producer of three terpenes, 2-methylisoborneol (2-MIB, 1), (+)-caryolan-1-ol (2), and (+)-1-epi-cubenol (3, Figure 1). The biosynthesis of 2 and 3 requires the action of well characterized terpene cyclases [1][2], while the biosynthesis of

• enzyme catalysis [34], but such approaches may not be suitable for terpenes that are in many cases unstable under acidic conditions or may tend to thermal rearrangements [35]. The successful formation of a completely deuterated natural product (up to 90% 2H) by fermentation has recently been reported for

• rhamnolipids in Pseudomonas and sophorolipids in Candida apicola [36], but no examples for completely deuterated terpenes with a deuterium content of >98% as presented here are known. In conclusion, fermentation in fully deuterated medium as performed in this work may offer a good and practicable approach to

Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus – conversion of selected spirocyclic terpenoids and computational analysis

• Verena Weidmann,
• Mathias Schaffrath,
• Holger Zorn,
• Julia Rehbein and
• Wolfgang Maison

Beilstein J. Org. Chem. 2013, 9, 2233–2241, doi:10.3762/bjoc.9.262

• olefinic precursors like terpenes or terpenoids. Biocatalytic variants have a large potential for industrial applications, particularly in the pharmaceutical and food industry. Herein we report efficient biocatalytic allylic oxidations of spirocyclic terpenoids by a lyophilisate of the edible fungus

• ; natural products; terpenes; Introduction Selective oxidations of CH-bonds are attractive synthetic transformations with a broad spectrum of applications in academia and a high impact on the industrial chemical value chain as they convert relatively cheap precursors into value-added products [1][2]. Among

• these transformations, allylic oxidations are of high interest because the olefinic starting materials are readily available as cheap bulk chemicals and many interesting derivatives such as terpenes are available from renewable sources [3][4][5]. In addition, the resulting allyl alcohols [6][7][8][9][10

A concise enantioselective synthesis of the guaiane sesquiterpene (−)-oxyphyllol

• Martin Zahel and
• Peter Metz

Beilstein J. Org. Chem. 2013, 9, 2028–2032, doi:10.3762/bjoc.9.239

• the total synthesis of the anticancer guaiane (−)-englerin A. A regio- and diastereoselective Co(II)-catalyzed hydration of the olefin and a transannular epoxide opening were used as the key reactions. Keywords: asymmetric synthesis; hydration; natural products; terpenes; transannular epoxide opening

Short synthesis of the common trisaccharide core of kankanose and kankanoside isolated from Cistanche tubulosa

• Goutam Guchhait and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 705–709, doi:10.3762/bjoc.9.80

• from C. tubulosa and have shown promising medicinal activity such as hepatoprotective and vasorelaxant activities [4][5][6]. Most of the compounds isolated from C. tubulosa and related species are phenylethyl oligosaccharides, iridoids, terpenes and lignans [4][5][6][7]. Recently, Yoshikawa et al

The volatiles of pathogenic and nonpathogenic mycobacteria and related bacteria

• Thorben Nawrath,
• Georgies F. Mgode,
• Bart Weetjens,
• Stefan H. E. Kaufmann and
• Stefan Schulz

Beilstein J. Org. Chem. 2012, 8, 290–299, doi:10.3762/bjoc.8.31

• of the production of volatiles by M. tuberculosis can facilitate the rational design of alternative and faster diagnostic measures for tuberculosis. Keywords: aromatic compounds; CLSA; terpenes; tuberculosis; volatile profile; Introduction Tuberculosis (TB) remains one of the most threatening

Novel fatty acid methyl esters from the actinomycete Micromonospora aurantiaca

• Jeroen S. Dickschat,
• Hilke Bruns and
• Ramona Riclea

Beilstein J. Org. Chem. 2011, 7, 1697–1712, doi:10.3762/bjoc.7.200

• methyl esters were identified. The identification of these esters from their mass spectra and retention indices, as well as the verification of the proposed structures by synthesis of representative reference compounds is presented. Besides several other compounds, such as terpenes, pyrazines, aromatic

Chimeric self-sufficient P450cam-RhFRed biocatalysts with broad substrate scope

• Aélig Robin,
• Valentin Köhler,
• Alison Jones,
• Afruja Ali,
• Paul P. Kelly,
• Elaine O'Reilly,
• Nicholas J. Turner and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2011, 7, 1494–1498, doi:10.3762/bjoc.7.173

• of their oxidation products. For instance, the terpenes α- and β-ionone and their derivatives have been widely used for the synthesis of carotenoids or in the fragrance industry [23][24][25][26], and functionalized aliphatic heterocycles are versatile building blocks for further elaboration, e.g., by

Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

• Silke Dubberke,
• Muhammad Abbas and
• Bernhard Westermann

Beilstein J. Org. Chem. 2011, 7, 421–425, doi:10.3762/bjoc.7.54

• the synthesis of natural occurring terpenes, i. a., trisporic acid and its derivatives. An advanced building block has been synthesized in a short reaction sequence, which involves an oxidative allylic rearrangement initiated by pyridinium dichromate (PDC) as the key step. Keywords: enzymatic

Control of asymmetric biaryl conformations with terpenol moieties: Syntheses, structures and energetics of new enantiopure C₂-symmetric diols

• Y. Alpagut,
• B. Goldfuss and
• J.-M. Neudörfl

Beilstein J. Org. Chem. 2008, 4, No. 25, doi:10.3762/bjoc.4.25

• : chiral diols; hydrogen bonds; axial chirality; terpenes; Introduction Enantiopure biaryl systems with flexible chiral axes are widespread, e.g. in pharmacological natural products or as ligands in enantioselective catalyses [1]. Chelating C2-symmetric diols such as BINOLs [2][3][4] and TADDOLs [5][6

Allylsilanes in the synthesis of three to seven membered rings: the silylcuprate strategy

• Asunción Barbero,
• Francisco J. Pulido and
• M. Carmen Sañudo

Beilstein J. Org. Chem. 2007, 3, No. 16, doi:10.1186/1860-5397-3-16

• exocyclic double bond joined to the cycloheptanone core is a structural feature very common in many naturally occurring terpenes (Scheme 11). Other allylsilane-based strategies have been recently developed to build up cycloheptane derivatives. Thus, the synthesis of seven membered hydroxycycloalkenes and