AbstractEs wird gezeigt, daß die Stereochemie der früher von den Autoren durch Abbaureaktion aus lris‐Öl erhaltenen Irone (I) und (II) ‐ deren Konfigurationszuordnung auf den Ergebnissen von Ruzicka et al. basierte und die die Enantiomeren der von anderen Autoren (vgl.

AbstractIn view of the demonstration by Janeicke et al. that different Iris varieties produce enantiomeric irones [6], we complement our 1971 paper on the stereochemistry of the irones [3]. (1) We give what information we have on the origin of the Iris oil used in [3]; (2) we sow that we and Ruzicka et al. on whose degradation work our determination of the C(2)‐configurations was based hd the same irones in hand; (3) we summarize independent assignments of the C(2)‐configurations and the relative configurations of the α‐irones. (4) We also describe the indentification of a trace of the missing trans‐γ‐irone in our oil, and (5) revise the preferred conformation of the cis‐α‐irones in solution.

AbstractAnhand einer ausführlichen mechanistischen Analyse der Reduktion der Titelverbindung (I) und auch ihrer deuterierten Derivate durch Li, Na oder K zu den Alkoholen (II) und (III) sowie ihren Alkoholaten und den außer mit Kebenfalls entstehenden Pinakolen wie hauptsächlich (IV) wird gefolgert, daß die Unterdrückung der Pinakolbildung, die bei einem Zusatz von NH4Cl eintritt, auf die Protonierung des intermediären Ketylradikals durch das NHZ‐Ion zurückzuführen ist.

AbstractA gas chromatographic investigation of the steam distilled oil of the herb of Artemisia vulgaris led to the identification of 21 irregular monoterpenes of non‐head‐to‐tail isoprenoid skeleton. The spectral data of some of these compounds are discussed. The structures of eight new irregular monoterpenes are given.

Ethyl (Z)‐4,7‐Octadienoate and (Z)‐3,5‐Hexadienyl Butyrate, two New Aroma Components of the Purple PassionfruitThe isolation of ethyl (Z)‐4,7‐octadienoate (1) and (Z)‐3,5‐hexadienyl butyrate (2), two new and important aroma constituents of the purple passionfruit (Passiflora edulis SIMS) is reported.Ester 1 was synthesized by two different routes: (1) via a Wittig reaction between the known 4‐oxobutyrate 4 and 3‐butenylidenephosphorane, and (2) by thermolysis of (Z)‐8‐acetoxy‐4‐octenoate 7 which was readily accessible from (Z,Z)‐1,5‐cyclooctadiene.Ester 2 was prepared from the known hex‐3‐yn‐5‐en‐1‐ol (8) by a stereoselective (Z)‐reduction of the triple bond to 9, using Rieke's active metallic zinc, followed by esterification.The organoleptic properties and the taste threshold values of 1 and 2 are given.

New Phellandrene Derivatives from the Root Oil of Angelica archangelica L.2‐Nitro‐1,5‐p‐menthadiene (5), trans‐ and cis‐6‐nitro‐1(7), 2‐p‐menthadiene (6 and 7), trans‐1(7), 5‐p‐menthadien‐2‐yl acetate (9) and a formal phellandrene derivative, 7‐isopropyl‐5‐methyl‐5‐bicyclo [2.2.2]octen‐2‐one (16), have been identified in the root oil of Angelica archangelica L. Starting from (−)‐(R)‐α‐phellandrene (1) (R)‐5, (4R, 6S)‐6/(4R, 6R)‐7, (2S, 4R)‐9 and (1R, 4R, 7R)‐16 as well as (2S, 4R)‐11, (2R, 4R)‐12 and (2R, 4R)‐10 have been prepared.

Abstract7‐Ionon (I) reagiert mit m‐Chlorperbenzoesäure zu den isomeren Epoxiden (II), die über die Anionen (III) zu den Bicyclen (IV) reagieren.

Plants have been the basis of many traditional medicines throughout the world for thousands of years and have continued to provide new remedies to mankind. They are one of the richest sources of bioactive compounds. The genus Passiflora comprises about 520 species of dicotyledonous plants in the family Passifloraceae. Passiflora edulis is also known as passion fruit, grenadelle, grenadine, passionflower, purple granadilla, or purple passion fruit. Native to southern Brazil, Paraguay to northern Argentina, P. edulis is a medicinal plant distributed in warm temperatures and tropical regions. In traditional system of medicines this species has a key role in management or treatment of various ailments. Properties traditionally recognized include anxiolytic, antiinflammatory, sedative, antioxidant, antispasmodic, antioxidant, and neuroprotective. This chapter aims to evaluate and comment on the scientific evidence regarding the therapeutic use and basis for future research on P. edulis, and its real potential for the development of the market for herbal medicinal products; to summarize the chemical constituents of therapeutic preparations; to analyze the pharmacological aspects of the plant by examining both preclinical and clinical research, and to assess the toxicity and safety profile.

Syntheses of Diastereoisomeric Caparrapi oxides.Two pathways have been developed for the synthesis of caparrapi oxide from the dihydroionones. The four diastereoisomeric racemates and their dehydro‐ and dihydro‐derivatives are described. NMR. spectra indicate that the sesquiterpene ethers having cis‐fused rings exist in two different conformations.

3-Methylthio-hexanol (3) and a mixture of cis- and trans-2-methyl-4-propyl-1, 3-oxathiane (6a and 6b) have been identified in a flavor concentrate of the yellow passion fruit of Hawaiian origin. Syntheses of these new flavor constituents are described.

Synthesis of alkyl‐5H‐cyclopenta[b]pyrazines.Alkyl‐5H‐cyclopenta[b]‐pyrazines (sometimes together with 5‐alkylidene‐5H‐6,7‐dihydrocyclopenta[b]pyrazines) are prepared by thermal degradation of 5‐acetoxy‐5H‐6,7‐dihydrocyclopenta[b]pyrazines; these are obtained by treatment of alkyl‐5H‐6,7‐dihydrocyclopenta[b]pyrazine N‐oxides with acetic anhydride. Cyclopenta[b]pyrazines which are potentially present in roasted food flavors possess interesting organoleptic properties.

AbstractThe unambiguous differences between the mass spectra of Z and E isomers of esters of 2‐methylbut‐2‐enoic acid enable the double bond geometry to be determined.

AbstractThe four geometrical isomers of 1,3,5‐undecatriene, 1a–d have been prepared (stereospecifically and non‐stereospecifically), using either (1) the Wittig reaction, (2) thermal sigmatropic hydrogen shifts, (3) partial reduction of triple bonds by zinc, or (4) organocopper reagents. The thermal behaviour of the four 1,3,5‐undecatrienes has been investigated and the products formed have been characterized. The spectra of 1a–d, and of related compounds, have been discussed in order to corroborate their configurational assignment.

AbstractNatural (+)‐davanone is 6S,7S,10R‐2,6,10‐trimethyl‐7,10‐oxidododeca‐2,11‐dien‐5‐one (1). Equilibration of davanone with base leads to the four possible isomers, but only a single deuterium atom is exchanged when deuterium oxide is the solvent.