Codonocarpus alkaloids—IV

Doskotch, Raymond W.; Fairchild, Edward H.; Hufford, Charles D.

doi:10.1016/s0040-4020(01)97494-0

Cited by 9 publications

(6 citation statements)

References 6 publications

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“…The main conformation of compound 1 most probably resembles a boat-chair geometry, as in melampolides, with C-14 below and C-15 above the plane of the medium ring. The evidence for this geometry, which has already been observed in tulirinol (20), is supported by the fact that, in addition to the nOe's mentioned above, there is another one "At 50.32 MHz in CDCl,/CD,OD (25°). bIn CDClj/CDjOD (57°).…”

supporting

confidence: 59%

“…The structure thus proposed for 1 corresponds to that of deacetyltulirinol (20). The limited resolution of the published 'H-nmr spectrum of this compound, however, especially as regards the signal of -1, does not permit a reliable comparison with our data.…”

mentioning

confidence: 56%

“…Furthermore, the available data suggest that compound 1 might also be identical with tatridin A, which had already been found in T. vulgare (21). The structure of this lactone, however, has not yet been definitively established, although there is evidence that it may be identical with deacetyltulirinol (20). Direct comparison of 1 (tic, nmr) with an authentic sample of tatridin A confirmed the identity of both compounds.…”

mentioning

confidence: 93%

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Nmr Studies of Tatridin A and Some Related Sesquiterpene Lactones from Tanacetum vulgare

Sanz¹,

Marco²

1991

J. Nat. Prod.

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supporting

confidence: 59%

mentioning

confidence: 56%

mentioning

confidence: 93%

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Nmr Studies of Tatridin A and Some Related Sesquiterpene Lactones from Tanacetum vulgare

Sanz¹,

Marco²

1991

J. Nat. Prod.

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Section: Introductionmentioning

confidence: 99%

“…However, diaryliodonium salts bearing halomethyl functionality have not been reported. In addition, literature precedent on the syntheses of diaryliodonium salts with formyl substituents is sparse 10−17 and in some cases has entailed the use of undesirable reagents, such as organomercury compounds 10,11 or strong acids 12,13 Here we report that variously functionalized diaryliodonium tosylates were readily accessed as their tosylates in moderate to high yields by generating a [hydroxy(tosyloxy)iodo]arene (HTIA) from a prepared (diacetoxyiodo)arene in situ for subsequent treatment with either an electron-rich arene or an arylstannane. This convenient methodology, as well as meeting our particular needs, will also be generally useful to others for preparing functionalized diaryliodonium salts for use as reagents or for their other potential applications (e.g., as photoinitiators or bactericides).…”

Section: ■ Introductionmentioning

confidence: 99%

Regiospecific Syntheses of Functionalized Diaryliodonium Tosylates via [Hydroxy(tosyloxy)iodo]arenes Generated in Situ from (Diacetoxyiodo)arenes

Chun

Pike

2012

J. Org. Chem.

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Ready access to 18F-labeled aryl synthons is required for preparing novel radiotracers for molecular imaging with positron emission tomography. Diaryiodonium salts react with cyclotron-produced no-carrier-added [18F]fluoride ion to produce [18F]aryl fluorides. We aimed to prepare functionalized diaryliodonium salts to serve as potential precursors for producing useful 18F-labeled aryl synthons, such as 18F-labeled halomethylbenzenes, benzaldehydes and benzoic acid esters. Such salts were designed to have one functionalized aryl ring, one relatively electron-rich ring, such as 4-methoxyphenyl or 2-thienyl, and a non-fluorine containing weakly nucleophilic anion. Generation of a [hydroxy(tosyloxy)iodo]arene from a functionalized (diacetoxyiodo)arene in situ followed by treatment with an electron-rich arene, such as anisole or thiophene, or with a functionalized arylstannane gave expedient regiospecific access to a wide range of functionally diverse diaryliodonium tosylates in moderate to high yields (44–98%). The described methodology broadens the scope for producing new functionalized diaryliodonium salts for diverse applications.

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A General Method for the Synthesis of Bastaranes and Isobastaranes: First Total Synthesis of Bastadins 5, 10, 12, 16, 20, and 21

Couladouros

Pitsinos

Moutsos

et al. 2004

Chemistry A European J

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A general strategy for the synthesis of twenty naturally occurring bastadins (all but bastadin 3) is presented. A key retrosynthetic disconnection of the two amide bonds, common in all target molecules, bisects the macrocyclic core into two diaryl ether fragments, an alpha,omega-diamine (western part) and an alpha,omega-dicarboxylic acid (eastern part). Efficient preparation of the synthetically challenging o-mono or dibromo-substituted diaryl ether linkages was achieved employing the diaryl iodonium salt method. Regarding the western part, variations of the aliphatic chain were more efficiently secured by the preparation of two different alpha,omega-aminonitrile moieties. Cobalt boride mediated reduction of the nitrile functionality established the required diamines and, at the same time, provided the necessary variation of the aromatic-ring bromination pattern. Regarding the eastern part, two different dicarboxyl precursors had to be prepared in order to accommodate bromination-pattern variations. Coupling and subsequent macrolactamization of different combinations of these key intermediates may lead at will to any member of this family of marine natural products. Four bastaranes (bastadins 5, 10, 12 and 16) and two isobastaranes (bastadins 20 and 21) were synthesized as a demonstration of the flexibility and efficiency of the approach presented.

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Codonocarpus alkaloids—IV

Cited by 9 publications

References 6 publications

Nmr Studies of Tatridin A and Some Related Sesquiterpene Lactones from Tanacetum vulgare

Nmr Studies of Tatridin A and Some Related Sesquiterpene Lactones from Tanacetum vulgare

Regiospecific Syntheses of Functionalized Diaryliodonium Tosylates via [Hydroxy(tosyloxy)iodo]arenes Generated in Situ from (Diacetoxyiodo)arenes

A General Method for the Synthesis of Bastaranes and Isobastaranes: First Total Synthesis of Bastadins 5, 10, 12, 16, 20, and 21

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