Efficient production of clerodane and ent-kaurane diterpenes through truncated artificial pathways in Escherichia coli

• Fang-Ru Li,
• Xiaoxu Lin,
• Qian Yang,
• Ning-Hua Tan and
• Liao-Bin Dong

Beilstein J. Org. Chem. 2022, 18, 881–888, doi:10.3762/bjoc.18.89

• diterpenoids are two categories of diterpenoids that are widely distributed in terrestrial plants, fungi, and a few bacteria and possess broad pharmacological bioactivities [1][2][3]. Representative natural products containing these skeletons are terpentecin (cytotoxic and antibiotic), salvinorin A (kappa

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

• Viola Kolaříková,
• Markéta Rybáčková,
• Martin Svoboda and
• Jaroslav Kvíčala

Beilstein J. Org. Chem. 2020, 16, 2757–2768, doi:10.3762/bjoc.16.226

• RCEYM of enynes leads to products containing a conjugated double bond system, which can undergo a Diels–Alder reaction and further can be employed in the synthesis of biologically active compounds, as for example cacospongiolide B [38], norsalvinorin A [39] or salvinorin A [40]. The substituted

Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems

• Katarina Kemper,
• Max Hirte,
• Markus Reinbold,
• Monika Fuchs and
• Thomas Brück

Beilstein J. Org. Chem. 2017, 13, 845–854, doi:10.3762/bjoc.13.85

• ], sclareol [69] and cis-abienol [64]. A biosynthesis study of salvinorin A (a psychotrophic agent with potential application as neuropsychiatric drug and for addiction treatment) in Salvia divinorum [70] resulted in the identification of five new Class I and Class II diterpene synthases. Moreover, this study

• performed in vivo substrate promiscuity tests following a combinatorial approach [41][66]. The resulting products entailed pimarane- and abietane-type diterpenes as well as the trans-clerodane type diterpene kolavenol, a putative intermediate in the salvinorin A biosynthesis. Other bifunctional diterpene

Studies toward bivalent κ opioids derived from salvinorin A: heteromethylation of the furan ring reduces affinity

• Thomas A. Munro,
• Wei Xu,
• Douglas M. Ho,
• Lee-Yuan Liu-Chen and
• Bruce M. Cohen

Beilstein J. Org. Chem. 2013, 9, 2916–2924, doi:10.3762/bjoc.9.328

• , unexpectedly, that the antagonist JDTic is a bivalent ligand: in addition to the orthosteric pocket occupied by morphinans, JDTic also occupies a distinct (allotopic) pocket. Mutagenesis data suggest that salvinorin A (1) also binds to this allotopic pocket, adjacent to the aspartate residue that anchors the

• for linked, fused or merged bivalent derivatives of 1. Keywords: allotopic; bivalent ligand; designed multiple ligand; JDTic; κ-opioid receptor; natural products; Salvinorin A; Introduction The structure–activity relationships of salvinorin A (1), a potent and selective κ (kappa) opioid, have been

• preparation and therapeutic use of salvinorin A derivatives (7,629,475 and 8,492,564). Binding affinities of salvinorin A (1) and furan derivatives for κ-OR [5]. Crystal structure of κ-OR in complex with JDTic compared to naltrindole’s binding pose in δ-OR. A: Cross-eyed stereoview of the crystal structure of

Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

• Sudipta Pathak,
• Kamalesh Debnath and
• Animesh Pramanik

Beilstein J. Org. Chem. 2013, 9, 2344–2353, doi:10.3762/bjoc.9.269

• reaction [15], a 6-endo-dig cyclization of heteroaryl esters to alkynes [16], or a Pd(II)-mediated cyclization of o-allylbenzaldehydes [17]. Salvinorin A, a natural product isolated from the hallucinogenic sage Salvia divinorum, which also contains a saturated isocoumarin ring, has been synthesized [18

8-epi-Salvinorin B: crystal structure and affinity at the κ opioid receptor

• Thomas A. Munro,
• Katharine K. Duncan,
• Richard J. Staples,
• Wei Xu,
• Lee-Yuan Liu-Chen,
• Cécile Béguin,
• William A. Carlezon Jr. and
• Bruce M. Cohen

Beilstein J. Org. Chem. 2007, 3, No. 1, doi:10.1186/1860-5397-3-1

• previously proposed indirect mechanism. Consistent with the general trend in related compounds, the title compound showed lower affinity at the kappa opioid receptor than the natural epimer salvinorin B (2a). The related 8-epi-acid 4b showed no affinity. Introduction Salvinorin A (1a), isolated from the

• -salvinorin A (1b).[12] Brown also reported that deacetylation of 1a under basic conditions gave 8-epi-salvinorin B (2b), but did not characterize either compound. Several further reports of epimerization at C-8 appeared over the following decade, [13][14] but no characterization data was presented. Valdés

• later identified the byproduct mentioned above as 8-epi-diol 3.[15] Characterization data was given, but the basis of the structure assignment was not stated. The first structure elucidation of one of these compounds was of 8-epi-salvinorin A (1b).[16] The trans-diaxial H-8 coupling constant found in