C. Miscellaneous Functions
179
This stereochemical feature was conclusively demonstrated by ozonolysis
of 34b to methyl hydrogen glutarate (35), and 2-acetoxyheptanoic acid (36a)
which was hydrolyzed to the corresponding ( — )-2-hydroxyheptanoic acid
(36b) of known absolute configuration (R).
^COaMe
(CH 2 ) 3
H0 2 C—CH—(CH 2 ) 4 —CH 3
N C0 2 H
36
35
a:R = Ac
b. R = H
The epimeric gorgonian-derived prostaglandins (34a,b) do not possess
the blood pressure lowering property of their mammalian counterparts.
It is not known what if any physiological effects the new prostaglandin
isomers exert on coelenterates, members of the phylum that produces them.
Schneider and co-workers (1972) have further examined the occurrence of
prostaglandins in the gorgonian P. homomalla and have found that some
specimens of this coelenterate do elaborate prostaglandins that possess the
active \5S configuration and others elaborate both R and S constituents.
Furthermore the Upjohn group (Bundy et al, 1972a) has isolated from the
same gorgonian a new prostaglandin (15.S)-15-hydroxy-9-oxo-5-/m«5',
lOjO-ira^-prostatrienoic acid (5-//*ö^-PGA 2 ), 37. Bundy et al. (1972b)
have also accomplished a laboratory transformation of the \5R to the \5S
configuration.
13
§
OH
37
TABLE 5.1
COMPOUNDS WITH UNBRANCHED CARBON SKELETONS
Text
mp (in
no.
Name
degrees)
0]£
References
1
/raws-1-(/raws-1-Hexenyl)- Oil
+77 ± 5
Moore et al. (1968)
2-vinylcyclopropane
(dictyopterene A)
2
trans,eis y cis-VnaQCSL-l ,3,
Oil
—
Pettus and Moore (1970)
5,8-tetraene
(continued)
c. Miscellaneous Functions
179
/C02 Me
(CH 2 )3
"C02H
3S
This stereochemical feature was conclusively demonstrated by ozonolysis
of 34b to methyl hydrogen glutarate (35), and 2-acetoxyheptanoic acid (36a)
which was hydrolyzed to the corresponding (- )-2-hydroxyheptanoic acid
(36b) of known absolute configuration (R).
OR
I
H0 2 C-CH-(CH 2 )4-CH 3
36
a: R = Ac
b:R = H
The epimeric gorgonian-derived prostaglandins (34a,b) do not possess
the blood pressure lowering property of their mammalian counterparts.
It is not known what if any physiological effects the new prostaglandin
isomers exert on coelenterates, members of the phylum that produces them.
Schneider and co-workers (1972) have further examined the occurrence of
prostaglandins in the gorgonian P. homomalla and have found that some
specimens of this coelenterate do elaborate prostaglandins that possess the
active 15S configuration and others elaborate both Rand S constituents.
Furthermore the Upjohn group (Bundy et af., 1972a) has isolated from the
same gorgonian a new prostaglandin (15S)-15-hydroxy-9-oxo-5-trans,
10,13-trans-prostatrienoic acid (5-trans-PGA 2 ), 37. Bundy et af. (1972b)
have also accomplished a laboratory transformation of the 15R to the 15S
configuration.
o
S
9 \""",'~C02H
lO~
#' IS
13
OH
37
TABLE 5.1
COMPOUNDS WITH UNBRANCHED CARBON SKELETONS
Text
no.
Name
mp (in
degrees)
[a]~
References
1
2
trans-1-(trans-1-Hexenyl)- Oil
2-vinylcyclopropane
(dictyopterene A)
trans,cis,cis-Undeca-1,3,
Oil
5,8-tetraene
+77 ± 5
Moore et at. (1968)
Pettus and Moore (1970)
(continued)
179
This stereochemical feature was conclusively demonstrated by ozonolysis
of 34b to methyl hydrogen glutarate (35), and 2-acetoxyheptanoic acid (36a)
which was hydrolyzed to the corresponding ( — )-2-hydroxyheptanoic acid
(36b) of known absolute configuration (R).
^COaMe
(CH 2 ) 3
H0 2 C—CH—(CH 2 ) 4 —CH 3
N C0 2 H
36
35
a:R = Ac
b. R = H
The epimeric gorgonian-derived prostaglandins (34a,b) do not possess
the blood pressure lowering property of their mammalian counterparts.
It is not known what if any physiological effects the new prostaglandin
isomers exert on coelenterates, members of the phylum that produces them.
Schneider and co-workers (1972) have further examined the occurrence of
prostaglandins in the gorgonian P. homomalla and have found that some
specimens of this coelenterate do elaborate prostaglandins that possess the
active \5S configuration and others elaborate both R and S constituents.
Furthermore the Upjohn group (Bundy et al, 1972a) has isolated from the
same gorgonian a new prostaglandin (15.S)-15-hydroxy-9-oxo-5-/m«5',
lOjO-ira^-prostatrienoic acid (5-//*ö^-PGA 2 ), 37. Bundy et al. (1972b)
have also accomplished a laboratory transformation of the \5R to the \5S
configuration.
13
§
OH
37
TABLE 5.1
COMPOUNDS WITH UNBRANCHED CARBON SKELETONS
Text
mp (in
no.
Name
degrees)
0]£
References
1
/raws-1-(/raws-1-Hexenyl)- Oil
+77 ± 5
Moore et al. (1968)
2-vinylcyclopropane
(dictyopterene A)
2
trans,eis y cis-VnaQCSL-l ,3,
Oil
—
Pettus and Moore (1970)
5,8-tetraene
(continued)
c. Miscellaneous Functions
179
/C02 Me
(CH 2 )3
"C02H
3S
This stereochemical feature was conclusively demonstrated by ozonolysis
of 34b to methyl hydrogen glutarate (35), and 2-acetoxyheptanoic acid (36a)
which was hydrolyzed to the corresponding (- )-2-hydroxyheptanoic acid
(36b) of known absolute configuration (R).
OR
I
H0 2 C-CH-(CH 2 )4-CH 3
36
a: R = Ac
b:R = H
The epimeric gorgonian-derived prostaglandins (34a,b) do not possess
the blood pressure lowering property of their mammalian counterparts.
It is not known what if any physiological effects the new prostaglandin
isomers exert on coelenterates, members of the phylum that produces them.
Schneider and co-workers (1972) have further examined the occurrence of
prostaglandins in the gorgonian P. homomalla and have found that some
specimens of this coelenterate do elaborate prostaglandins that possess the
active 15S configuration and others elaborate both Rand S constituents.
Furthermore the Upjohn group (Bundy et af., 1972a) has isolated from the
same gorgonian a new prostaglandin (15S)-15-hydroxy-9-oxo-5-trans,
10,13-trans-prostatrienoic acid (5-trans-PGA 2 ), 37. Bundy et af. (1972b)
have also accomplished a laboratory transformation of the 15R to the 15S
configuration.
o
S
9 \""",'~C02H
lO~
#' IS
13
OH
37
TABLE 5.1
COMPOUNDS WITH UNBRANCHED CARBON SKELETONS
Text
no.
Name
mp (in
degrees)
[a]~
References
1
2
trans-1-(trans-1-Hexenyl)- Oil
2-vinylcyclopropane
(dictyopterene A)
trans,cis,cis-Undeca-1,3,
Oil
5,8-tetraene
+77 ± 5
Moore et at. (1968)
Pettus and Moore (1970)
(continued)