Natural and directed biosynthesis of communesin alkaloids

Wigley, Lucy J.; Mantle, Peter G.; Perry, David A.

doi:10.1016/j.phytochem.2005.10.011

Cited by 52 publications

(28 citation statements)

References 16 publications

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“…As an outgrowth of our investigations in the area of calycanthaceous alkaloids, 8,9 we sought to develop a unified and convergent approach to the communesin alkaloids. We drew inspiration from a speculated biogenesis involving the stereocontrolled oxidative union of two dissimilar tryptamine derivatives followed by reorganization of a C3a–C3a′ linked heterodimer, 10,11,12,13 reminiscent of the pathways leading to the related calycanthoids. 12,14, While our biosynthetic considerations were purely hypothetical at the outset of this synthesis campaign, Houk, Garg, and Tang have recently disclosed 15 incisive biosynthetic and computational studies that echo the key transformations developed in our synthesis.…”

Section: Introductionmentioning

confidence: 99%

Convergent and Biomimetic Enantioselective Total Synthesis of (−)-Communesin F

et al. 2016

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The first biomimetic enantioselective total synthesis of (−)-communesin F based on a late-stage heterodimerization and aminal exchange is described. Our synthesis features the expedient diazene–directed assembly of two advanced fragments to secure the congested C3a–C3a′ linkage in three steps, followed by a highly efficient biogenetically inspired aminal reorganization to access the heptacyclic communesin core in only two additional steps. Enantioselective syntheses of the two fragments were developed, with highlights including the catalytic asymmetric halocyclization and diastereoselective oxyamination reactions of tryptamine derivatives, a stereoselective sulfinimine allylation, and an efficient cyclotryptamine–C3a-sulfamate synthesis by either a new silver–promoted nucleophilic amination or a rhodium–catalyzed C–H amination protocol. The versatile synthesis of the fragments, their stereocontrolled assembly, and the efficient aminal–exchange as supported by in situ monitoring experiments, in addition to the final stage N1′-acylation of the communesin core provide a highly convergent synthesis of (−)-communesin F.

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Section: Introductionmentioning

confidence: 99%

Convergent and Biomimetic Enantioselective Total Synthesis of (−)-Communesin F

et al. 2016

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“…Isotope feeding experiments showed that both indoles originated from 1 . 94 One of the incorporated indole moiety is prenylated at C4 and has remained intact. Stoltz et al proposed that (-)-aurantioclavine ( 55 ), an ergot-like molecule derived from 5 , is a building block that serves as the prenylated half of the communesin structure ( Scheme 7 ).…”

Section: Biosynthetic Categories Of Indole Alkaloidsmentioning

confidence: 99%

Biosynthesis of fungal indole alkaloids

2014

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This review provides a summary of recent research advances in elucidating the biosynthesis of fungal indole alkaloids. Different strategies used to incorporate and derivatize the indole/indoline moieties in various families of fungal indole alkaloids will be discussed, including tryptophan-containing nonribosomal peptides and polyketide-nonribosomal peptide hybrids; and alkaloids derived from other indole building blocks. This review also includes discussion regarding the downstream modifications that generate chemical and structural diversity among indole alkaloids.

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“…The progress of reaction was registered spectrophotometrically by measuring the increase of absorbance of the oxidised form of ABTS at  = 410 nm at 1 min intervals for 20 min. H]-tryptamine was synthesised by enzymatic decarboxylation of 5-F--L-Trp, respectively, using the modifi ed procedures described earlier [21]. The decarboxylation of 5-F--L-Trp was carried out using fully deuteriated and buffered medium, corrected to pD 5.5 due to higher pK (D 2 O) [22].…”

Section: Kinetic Assaysmentioning

confidence: 99%

Enzymatic oxidation of substituted tryptamines catalysed by monoamine oxidase

Dragulska

Kańska

2014

Nukleonika

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Abstract. The enzymatic deamination of 5-fl uorotryptamine and 5-hydroxytryptamine, 5-HT, catalysed by enzyme monoamine oxidase A (MAO-A, EC 1.4.3.4) was investigated using the kinetic (KIE) and solvent (SIE) isotope effects methods. The numerical values of deuterium isotope effects in the (1R) positions of 5-F-tryptamine were determined using non-competitive spectrophotomeric method. Isotopologue 5-F-[(1R)--2 H]-tryptamine, needed for kinetic studies was obtained by enzymatic decarboxylation of 5-fl uoro-L-tryptophan, 5-F-L-Trp, in fully deuteriated medium.

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Natural and directed biosynthesis of communesin alkaloids

Cited by 52 publications

References 16 publications

Convergent and Biomimetic Enantioselective Total Synthesis of (−)-Communesin F

Convergent and Biomimetic Enantioselective Total Synthesis of (−)-Communesin F

Biosynthesis of fungal indole alkaloids

Enzymatic oxidation of substituted tryptamines catalysed by monoamine oxidase

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