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Saidkhodzhaeva, Sh. A.; Bessonova, I. A.; Абдуллаев, Н. Д.

doi:10.1023/a:1014479628541

Cited by 23 publications

(14 citation statements)

References 8 publications

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“…Spectroscopic data of the synthetic arcutinine ( 2 ) were identical to those reported for the natural product, except for the carbon chemical shift of the carbonyl group in the isobutyryl moiety (synthetic δ C = 176.98 vs reported δ C = 175.80) . In the isolation paper, the natural products arcutine ( 1 ) and arcutinine ( 2 ) were isolated as an inseparable mixture in a 2:1 ratio . However, the carbon chemical shift of both the carbonyl groups in 1 and 2 were assigned to be the same (δ C = 175.80).…”

Section: Results and Discussionmentioning

confidence: 99%

“…The arcutine-type C 20 -diterpenoid alkaloids (Figure ) are structurally characterized by a congested hexacyclic framework, including a challenging tetracyclo[5.3.3.0 4,9 .0 4,12 ]tridecane ring system (BCDF rings, highlighted with blue bonds) and a unique azabicyclo[4.3.0]nonane unit (AE rings), as well as three all-carbon quaternary stereogenic centers (C4, C5, and C8) . Biogenetically, the arcutine alkaloids could be derived from the hetidine core through a C20 (10 → 5) rearrangement event (Figure A). , The representative arcutine-type molecules ( 1 and 2 , Figure B) were first isolated by Saidkhodzhaeva and co-workers from Aconitum arcuatum , while arcutinidine ( 3 ) was obtained as a saponification product through chemical transformation from 1 and 2 . More recently, aconicarmicharcutinium A ( 4 ) was reported by Shi and co-workers from Aconitum carmichaelii .…”

Section: Introductionmentioning

confidence: 99%

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Enantioselective Total Synthesis of (−)-Arcutinine

et al. 2019

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The first total synthesis of an arcutine-type C20-diterpenoid alkaloid arcutinine has been achieved in both racemic and asymmetric forms. Construction of the C4 quaternary center and the pyrrolidine E ring in an early stage proved to be important for achieving the successful synthesis of the target alkaloid. Strategically, an asymmetric conjugate addition/aldol cascade and a decarboxylative allylation reaction allowed the establishment of the vicinal all-carbon quaternary stereocenters at C4 and C5. Furthermore, a sequence consisting of an intramolecular aza-Wacker cyclization, an oxidative dearomatization/intramolecular Diels–Alder cycloaddition cascade, and a ketyl-olefin cyclization enabled the assembly of the core structure and led to the total synthesis of arcutinine.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enantioselective Total Synthesis of (−)-Arcutinine

et al. 2019

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“…Arcutinidine ( 20a ), arcutinine ( 20b ), and arcutine ( 20c ), isolated from Aconitum arcuatum , belong to C 20 -diterpenoid alkaloids. , Biogenetically, it was proposed that they are derived from hetidine type alkaloids via WM rearrangement (Scheme ). , …”

Section: 2-shift In Domino Processesmentioning

confidence: 99%

Natural Product Synthesis Enabled by Domino Processes Incorporating a 1,2-Rearrangement Step

Delayre

Wang

2021

ACS Cent. Sci.

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The art of natural product total synthesis is closely associated with two major determinants: the development/application of novel chemical reactions and the innovation in strategic use of classic organic reactions. While purposely seeking/applying a new synthetic methodology allowing nonconventional bond disconnections could shorten the synthetic route, the development of domino processes composed of a series of well-established reactions could also lead to a concise, practical, and aesthetically appealing synthesis. As an important class of textbook reactions, the 1,2-anionotropic rearrangements discovered at the dawn of modern organic chemistry have important bearings not only on chemical synthesis but also on the conceptual breakthroughs in the field. In its basic form, the 1,2-shift affords nothing but a constitutional isomer of the starting material and is therefore not a complexity-generating transformation. However, such a simple 1,2-shift could in fact change the molecular topology if the precursor is cleverly designed. More dramatically, it can metamorphosize the structure of the substrate when it is combined with other transformations in a domino sequence. In this Outlook, we highlight recent examples of natural product synthesis featuring a key domino process incorporating a 1,2-anionotropic rearrangement. Specifically, domino reactions integrating Wagner−Meerwein, pinacol, α-ketol, α-aminoketone, α-iminol, or benzilic acid rearrangements will be discussed.

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“…(À)-Arcutinine was rst isolated by Saidkhodzhaeva and co-workers from Aconitum arcuatum. 40 Yong Qin and co-workers realized the rst asymmetric synthesis of (À)-arcutinine using the Stahl aza-Wacker cyclization reaction 41 as a key step (Fig. 33).…”

Section: Enantioselective Synthesis Of (à)-Arcutininementioning

confidence: 99%