Glycals in stereochemical synthesis

Enantiomerically pure (14R)-14-methylhexadeca-8Z-enal (cis-trogodermal) — the aggregation pheromone of the khapra beetle (Trogoderma) — and its (14S,8Z)-enantiomer has been effected from di-O-benzoyl-D- and -L-arabinals.Institute of Chemistry, Bashkir Branch, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 707–712, September–October, 1991.     

Triterpene glycosides from the holothurian Cucumaria frondosa

Two triterpene glycosides have been isolated from an alcoholic extract of the holothurianCucumaria frondosa collected in the Kola littoral, Barents Sea: the main component of the glycoside fraction — frondoside A (I) — and a minor component — frondoside A₁ (II).Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Russian Academy of Sciences, Vladivostok. Murmansk Marine Biological Institute. Russian Academy of Sciences, Dal'nie Zelentsy, Murmansk province. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 260–263, March–April, 1993.     

Triterpene glycosides of Gypsophila patrinii III. The structure of philoside B

Summary The structure of philoside B — a gypsogenin nonaoside isolated from the roots ofGypsophila patrinii — has been established.A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan'Branch, Academy of Sciences of the USSR. Correspondence Institute of Soviet Commerce. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 603–607, September–October, 1974.     

Structure of stachysolone

Summary It has been shown that stachysolone — a bitter substance fromStachys annua L. — is a diterpenoid with a rearranged labdane hydrocarbon skeleton of the kolavane type. Structural formula (I) has been established for stachysoloneInstitute of Chemistry, Academy of Sciences of the Moldavian SSR. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czechoslovakian SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 295–299, May–June, 1972.     

Synthesis of (E)-dodec-3-en-1-yl acetate — The main component of sex pheromones of Scrobipalpa ocellatella and Scrobipalpopsis solanivora

(E)-Dodec-3-en-l-yl acetate — the main component of the sex pheromones ofScrobipalpa ocellatella andScrobipalpopsis solanivora — has been obtained by a three-stage synthesis from decanal and malonic acid. The overall yield of pheromone was 33% calculated on the initial aldehyde.A. S. Sadykov Institute of Bioorganic Chemistry, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 682–683, September–October, 1988.     

Insect pheromones and their analogues. XLVI. Synthesis of 13RS-hydrooxytetradec-5Z-enoic acid — The acyclic precursor of the macrolide component of the pheromone of Cryptolestes pusillus

New routes for the synthesis of 13RS-hydroxytetradec-5Z-enoic acid — the acyclic precursor of the macrolide component of the pheromone ofCryptolestes pusillus have been developed on the basis of the readily accessible 1-methylcycloocta-1Z, 5Z-diene or isopropyl nona-3E,8-dienoate.Institute of Biological Plant Protection, Moldovian Academy of Sciences, Kishinev. Scientific-Research Institute of Forestry and Forestry Mechanization, Pushkino. Moscow Institute of Wood Technology; and Georgia Institute of Mountain Forestry, Tbilisi. Translated from Khimiya Prirodnykh Soedeninii, No. 1, pp. 150–155, January–February, 1993.     

Insect pheromones and their analogs. XLVII. Synthesis of 11-oxododeca-3,6-diynoic acid — The acyclic precursor of a macrolide component of pheromones of Oryzaephilus mercator and O. Surinamensis

A new approach is proposed to the synthesis of 11-oxododeca-3,6-diynoic acid — the acyclic precursor of a macrolide component of pheromones ofOryzaephilus mercator andO. surinamensis — from the readily available tetrahydropyran or allylacetone via the intermediate 5-bromo-2,2-ethylenedioxypentane.Institute of Organic Chemistry, Urals Division, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 288–292, March–April, 1993.     

Synthesis of dodec-5E-en-1-ol — The pheromone of Tricimba cincta — And tetradec-5E-1-yl acetate — An imitator of the pheromone of Rhynchopacha sp.

On the basis of a modified Knoevenagel reaction starting from octanol and decanal, the stereodirected synthesis has been effected of dodec-5E-en-ol (the pheromone of the grass flyTricimba cincta — and tetradec-5E-en-yl acetate) an imitator of the pheromone of the mothRhynchopacha sp. A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 129–132, January–February, 1991.     

New glycosides from the holothurian Cucumaria japonica

Four new compounds have been isolated from the fraction of weakly polar triterpene glycosides of the holothurianCucumaria japonica: cucumariosides A₁-2 (I), A₀-1 (II), A₀-2 (III), and A₀-3 (IV). The structures of these substances have been established by chemical and physical methods.Deceased.Pacific Ocean Institute of Bioorganic Chemistry, Far-Eastern Scientific Center, Russian Academy of Sciences, Vladivostok. Institute of Chemistry of Plant Substances, Uzbekistan Republic Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 242–248, March–April, 1993.     

Proanthocyanidins of Rhodiola semenovii

The structures of two compounds previously isolated fromRhodiola semenovii, rhodokhinoside (I) and rhodikhim (II), have been established.Institute of the Chemistry of Plant Substances, Uzbek. Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 771–777, November–December, 1991.     

Triterpene glycosides of Gypsophila patrinii II. The structure of philoside A

Summary From the roots ofGypsophila patrinii two high-molecular-weight triterpene glycosides have been isolated — philosides A and B. The structure of philoside A has been established; it is a gypsogenin nonaoside.A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan' Branch, Academy of Sciences of the USSR. Correspondence Institute of Soviet Commerce. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 598–603, September–October, 1974.     

Pheromones of insects and their analogs

From cyclohexene and caproaldehyde, using ozonolysis and the Knoevenagel reaction, we have synthesized hexadeca-7Z,11E-dien-l-yl acetate — the sex pheromone ofSitotroga cerealella and a component of the sex pheromone ofPectinophora gossypiella.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 704–707, September–October, 1991.     

Triterpene glycosides of Dianthus deltoides II. Structure of dianthoside C

Summary The structure of dianthoside C — a triterpene glycoside fromDianthus deltoides L. — has been established.A. E. Arbuzov Institute of Organic and Physical Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 420–425, July–August, 1971.     

Insect pheromones and their analogues

A scheme has been developed for the synthesis of (R)-(–)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata) using as the chiral synthon (R)-(+)-methylheptenal obtained by the hydroperoxide oxidation of the readily available (S)-(+)-dihydromyrcene.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 125–129, January–February, 1992.     

The structure of nutanoside

Summary The complete structure of nutanoside — a triterpene glycoside isolated from the roots ofSilene nutans L. — has been established.A. E. Arbuzov Institute of Organic and Physical Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 412–416, July–August, 1971.     

Structure of artabin

Summary FromArtemisia absinthium L. a new sesquiterpene lactone of the germacrane type — artabin — has been isolated. Structure I is proposed for it.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedineii, No. 6, pp. 691–694, November–December, 1970.     

Triterpene glucosides of Dipsacus azureus. III. Structure of dipsacobioside

A new triterpene glycoside — dipsacobioside — has been isolated from the root of theDipsacus azureus Schrenk. By chemical transformation and spectral methods its structure has been established as hederagenin 3-O-[O--L-rhamnopyranosyl-(14)--L-arabinopyranoside].Institute of Organic Chemistry, Kirgiz SSR Academy of Sciences, Frunze. Institute of the Chemistry of Plant Substances, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 204–207, March–April, 1989.