Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• along with a large suite of related molecules, the taxanes [17]. This pathway promiscuity can be illustrated with another popular example of a terpene family: the cannabinoids, with more than 100 members used for both medical and recreational purposes. While its most prominent member (−)-trans-Δ

Assembly of fully substituted triazolochromenes via a novel multicomponent reaction or mechanochemical synthesis

• Robby Vroemans,
• Yenthel Verhaegen,
• My Tran Thi Dieu and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 2689–2697, doi:10.3762/bjoc.14.246

• -triazole; Introduction Chromenes are important structural motifs and are omnipresent in nature and drugs for medicinal applications [1][2][3][4]. Vitamin E [5][6][7][8], arahypin-5 [9][10], THC and other cannabinoids [11][12][13][14] are only a few examples of biologically relevant chromenes. Hence, the

Characterization of the synthetic cannabinoid MDMB-CHMCZCA

• Carina Weber,
• Stefan Pusch,
• Dieter Schollmeyer,
• Sascha Münster-Müller,
• Michael Pütz and
• Till Opatz

Beilstein J. Org. Chem. 2016, 12, 2808–2815, doi:10.3762/bjoc.12.279

• cannabinoids; VCD spectroscopy; Introduction Starting in 2008 with the appearance of “Spice products”, herbal mixtures spiked with synthetic cannabinoid receptor agonists began to spread on the international drug market [1][2]. The cannabimimetic substances are the psychoactive ingredients of those mixtures

• Chiralpak IA-3 column (length: 25 cm, diameter: 4.6 mm, particle size: 3 μm; Daicel) was used at a temperature of 40 °C. Synthetic cannabinoids JWH-018 (1), MDMB-CHMICA (2), MDMB-CHMCZCA (3), and EG-018 (4). Molecular structure of (S)-MDMB-CHMCZCA (3) with numbering scheme. ESI-MSn pattern of 3 (m/z values

Highly enantioselective access to cannabinoid-type tricyles by organocatalytic Diels–Alder reactions

• Stefan Bräse,
• Nicole Volz,
• Franziska Gläser and
• Martin Nieger

Beilstein J. Org. Chem. 2012, 8, 1385–1392, doi:10.3762/bjoc.8.160

• synthesis. Keywords: cannabinoids; Diels–Alder reaction; natural product synthesis; organocatalysis; Introduction The Diels–Alder reaction is one of the most important processes for carbon–carbon-bond formation in organic chemistry [1][2]. Especially in the synthesis of natural products it is a widely

Aroylketene dithioacetal chemistry: facile synthesis of 4-aroyl- 3-methylsulfanyl- 2-tosylpyrroles from aroylketene dithioacetals and TosMIC

• H. Surya Prakash Rao and
• S. Sivakumar

Beilstein J. Org. Chem. 2007, 3, No. 31, doi:10.1186/1860-5397-3-31

• of the cannabinoids. [14] In continuation, and by following the method presently developed, the trisubstituted pyrrole 7 having pyrenoyl substituent was synthesized from AKDTA 6 (Scheme 3). Initially, 1-acetylpyrene 5 was transformed to hitherto unknown pyrene based AKDTA 6 by reaction with carbon