RESEARCH ON ALKALOIDS OF HELIOTROPIUM LASIOCARFUN: STRUCTURE OF BELIOTRINE

• Document Type: CREST
• Collection: General CIA Records
• Document Number (FOIA) /ESDN (CREST): CIA-RDP80-00809A000600270334-1
• Release Decision: RIPPUB
• Original Classification: C
• Document Page Count: 3
• Document Creation Date: December 22, 2016
• Document Release Date: September 19, 2011
• Sequence Number: 334
• Publication Date: December 12, 1949
• Content Type: REPORT

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CLASSIFICATION CYIET'mNi'IYL ~~~~
CENTRAL INTELLIGENCE AGENG k%T
INFORMATION FROM
W U N I USCiR
SUBJECT Scientific - Chemistry
HOW
PUBLISHED Monthly periodical
WHERE
PUBLISHED Moscow/Leningrad
DATE
PUBLISHED Sep 1949
LANGUAGE Russian
"IS DOOONDFTIMNTATND INTOANATION A/ITCTIND TU NADDNAA DN/NNTN
OF TN[ ONITND NATND DITNIN TWI NUND, DI DDMDDA.D ACT N
N. D. C.. DI AND U. AM Afl UDEN. ITS TNANNONION M us DDTDAATMN
Or 115 CONTDNTT I. LIT NAN.IR TO AD DNANTNONIIDTD IANDON IN .DO-
NUTNO DT MW. NnnODDiflot OF moo IONN ID TMNIDITN.
THIS IS UNEVALUATED INFORMATION
Zhurnal Obshchey. lfhimii, Vol RISC, No 9, 149.
RESNARCH ON ALSAL0IDe3 OP ffiIOTROPlUM LASIOCARPUl9:
8ilQlf.`iuns or (-mw
G. P. Men'ahikov
A. D. Hhtotkov
Phytocbm
All-Union Sci Res t ieophar I nt
imeni Sergey Ordzhonikidze
Submitted 31 May 1948
Prewar work on heliotrine by the en+14*rs left only the position of the
two hydroxyl groups and the double fond or heliotridises (an aminoglycol formed
during the hydrolysis of the alkaloid) to be cleared up.
To accomplish this, the amino alcohol ox3beliotridane (C80-15g09), product
of the catalytic reduction of heliotrine, was oxidised to prodocb an amino
ketone (C811 13ON) identical with retronecanol. Since retronecanol has the
structure of a 1-methyl-6-ketopyrrolizidine, ox hellotridane should helm
the folioving structure:
NO r
In this manner the position of the reduction-resistant hydroxyl group of
heliotr$dine was established.
An amino alcohol, identical with isoretronecanol, and leaving the fol-
loving structure:
-11~0WEIBEINTIAIN
CLASSIFICATION
1STATE ._ .. NAW 1X I Ns
CJIe MXII1'IAL
mcTPIaI mnu
A
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 Sanitized Copy Approved for Release 2011/09/19: CIA-RDP80-00809A000600270334-1
CH.,OH
was prepared by elimination of the secondary bydrotryl group and the double
bond of heliotridine. In this manner the position of the secondary hydroxyl
group of heliotridine vqs determined (this group being usresistant to reduction
When only the secondary hydroxyl group of beliotridine was eliminated,
supi.nidine, an unsaturated amino alcohol, was obtained. The structure of
supinidine, also given in a previous article, is:
CH2 0 H
N "T
From this it was deduced that the double bond of beliotridine should be be-
tveen the first and the second carbon atoms of the pyrrolizidine ring.
and hellotrine itself (previously described from knowledge of the structure
of heliotrinic acid) should have the structure:
C /f H3
CH
I
HO-CH- ~H- C -CH2O -CO -C-OH
i I ~I I
C L\ /\ / H H-ocH3
CH2 CH2 CH3
CONFIDEUTIAL
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1. G. P. Mer.'eb1kov, Her., Vol 65, p 974 (1932)..
2. G. P. Men'shikov, Izv. Aksd. Nauk SSB, seriya khtm., Vol 7, p 1,035 (1937).
3. R. Adams, Rogers, J. Am. Soc., Vol 63, p 228 1194.1).
4. G. P. Mem'shikov, 7hOKh, Vol 9, p 1,852 (1939)-
5. G. P. Men"sbikov, Bar., Vol 68, p 1,051 (1935)-
6. Willataetter, Der., Vol 29, P 396 (1896).
7. R. Adams, K. Ea bin, J. An. Soc., Vol 64, P 2,597 (1942).
B. R. A. Sonovalova, A. P. Orekhov, Lh0K , Vol 8, P 396 (1938)?
9. R. Adams, N. Leonard, J. An. Soc., Vol 66, P 257 (1944).
10< G. ftrgerm, J. Chi. Sac., 1935, 11-
11. G. P. Meza'shikov, Ye. L. Gurevich, Issledovaulye alkaloidov
Heliotropimm supimmm, I (Research on the Alkaloids of Sellotroplua
Supimm, 1), ZIOKh, Vol 19, P 1,382 (1949)
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