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Showing papers on "Total synthesis published in 1968"



Journal ArticleDOI
TL;DR: In this article, the total synthesis of the biologically active macrolide zearalenone together with its optical resolution and the determination of its absolute configuration as "S" are described.

96 citations





Journal ArticleDOI
TL;DR: Structural work culminated in the structure and absolute stereochemistry shown in (I) for the alkaloid Lycopodine, and the identical expression (II) can be written as in the twodimensional representation (III).
Abstract: Numerous alkaloids have been isolated over the years from the genus Lycopodium. Among these, Lycopodine first isolated in 18811, seems to be the most widely distributed2. Structural work, ranging over a number of years, culminated in the structure and absolute stereochemistry shown in (I) for the alkaloid2. The identical expression (II) can be written as in the twodimensional representation (III).

52 citations




Journal ArticleDOI
TL;DR: In this article, the dextrorotatory enantiomer (+)4 was converted in a 5-step stereospecific total synthesis to the important BCD tricyclic intermediate (−)13.

43 citations




Journal ArticleDOI
TL;DR: Podocarpic arid was converted to taxodione and since the total synthesis of the former is recorded, this conversion implies a totalhesis of the latter.



Journal ArticleDOI
TL;DR: A free dotriacontapeptide amide was obtained whose physical, chemical and biological behaviour was indistinguishable from that of the natural hormone.
Abstract: A total synthesis of hog thyrocalcitonin is described. A protected C-terminal tridecapeptide amid (20–32) was coupled with a protected central decapeptide (10–19), and the resulting protected tricosapeptide amide (10–32) was reacted with the N-terminal protected nonapeptide (1–9). After elimination of the protective groups, a free dotriacontapeptide amide was obtained whose physical, chemical and biological behaviour was indistinguishable from that of the natural hormone.





Journal ArticleDOI
TL;DR: In this article, condensation of 3-hydroxyphenethylamine with carbonyl compounds led to the total synthesis of (±)-coreximine and spiro[cycloalkane-1,1′-isoquinoline] derivatives.
Abstract: Novel syntheses of 1-substituted isoquinoline and spiro[cycloalkane-1,1′-isoquinoline] derivatives were achieved by condensation of 3-hydroxyphenethylamine with carbonyl compounds, and application of this method led to the total synthesis of (±)-coreximine.

Journal ArticleDOI
TL;DR: In this paper, a total synthesis of (±)1β,4a-α-dimethyl-cis-1,2,3,4,4α,9a-hexahydrofluoren-9-one-1 1α-carboxylic acid (II) has been described.


Journal ArticleDOI
TL;DR: An 11-step process for total synthesis of dl-PGB1 (prostaglandin B1) is described and the chemical structure of each interim step in the process is presented.
Abstract: An 11-step process for total synthesis of dl-PGB1 (prostaglandin B1) is described. The chemical structure of each interim step in the process is presented. The following analytical data were obtained for each new compound in the process: 1) ultraviolet absorption spectra in methanol; 2) infrared absorption spectra in chloroform; and 3) NMR spectra in deuterochloroform.

Patent
22 Nov 1968
TL;DR: In this article, a facile total synthesis of 19β-alkyl-C/D-trans-steroidal materials was obtained via a unique asymmetric induction followed by subsequent stereospecific reaction steps.
Abstract: The novel intermediates and processes of this invention provide a new synthetic route for the preparation of pharmaceutically valuable 19-norsteroids. Further, the intermediates and processes of the invention provide a novel route for the preparation of pharmaceutically valuable estrones. The present invention provides a facile total synthesis of 19β-alkyl-C/D-trans-steroidal materials. This desirable result is obtained via a unique asymmetric induction followed by subsequent stereospecific reaction steps. As a precursor to the steroidal Ring A, a 3,5-disubstituted-4-isoxazolylmethylene group is employed in this synthesis.






Journal ArticleDOI
TL;DR: It is concluded that this synthesis is not a practical method for synthesis of PGE1 or PGF1 alpha but with modifications the technique can yield PGB1.