A practical, enantiospecific synthesis of (S)-trans-γ- monocyclofarnesol

Natural Product Communications

Volumn 7, Issue 12, 2012, Pages 1569-1572

  Serra, Stefano ^a  

^a CNR   (Italy)

Author keywords

Enzyme mediated resolution; Fractional crystallization.; Horner Wadsworth Emmons reaction; Sesquiterpenes; Stereoselective synthesis

Indexed keywords

ACETOXY GAMMA IONONE; AGELASINE E; ALPHA IONONE; DEHYDROAMBLIOL A; ETHYL 5 (2,2 DIMETHYL 6 METHYLENECYCLOHEXYL) 3 METHYLPENT 2 ENOATE 5; ETHYL 5 (2,2 DIMETHYL 6 METHYLENECYCLOHEXYL) 3 METHYLPENT 2 ENYL 3,5 DINITROBENZOATE; FARNESOL; GAMMA DIHYDROIONONE; GAMMA MONOCYCLOFARNESYL ETHYL ESTER; LUFFARIN W; PHENAZINOMYCIN; TERPENOID; TRIXAGOL; UNCLASSIFIED DRUG; (S) TRANS GAMMA MONOCYCLOFARNESOL; (S)-TRANS-GAMMA-MONOCYCLOFARNESOL; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; NORISOPRENOID; SESQUITERPENE;

ARTICLE; BIOSYNTHESIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; DEGRADATION KINETICS; FRACTIONAL CRYSTALLIZATION; HORNER WADSWORTH EMMONS REACTION; HYDROLYSIS; ISOMER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PURIFICATION; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY; CHEMISTRY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; STEREOISOMERISM; SYNTHESIS;

CHROMATOGRAPHY, THIN LAYER; CRYSTALLIZATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYDROGEN-ION CONCENTRATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; NORISOPRENOIDS; SESQUITERPENES; STEREOISOMERISM;

MLCS; MLOWN;

EID: 84875047418     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x1200701205     Document Type: Article

References (14)

1. Suzuki KT, Suzuki N, Nozoe S. (1971) Isolation and enzymic formation of trans-γ-monocyclofarnesol. Journal of the Chemical Society D: Chemical Communications, 527.
2. Toyota M, Ooiso Y, Kusuyama T, Asakawa Y. (1994) Drimane-type sesquiterpenoids from the liverwort Diplophyllum serrulatum. Phytochemistry, 35, 1263-1265.
3. De Pascual Teresa J, Caballero E, Caballero C, Medarde M, Barrero AF, Grande M. (1978) Trixagol, natural γ-cyclogeranyl-geraniol from Bellardia trixago (L.) All. Tetrahedron Letters, 19, 3491-3494.
4. Walker RP, Faulkner DJ. (1981) Diterpenes from the sponge Dysidea amblia. Journal of Organic Chemistry, 46, 1098-1102.
5. Butler M, Capon R. (1992) The Luffarins (A-Z), novel terpenes from an Australian marine sponge, Luffariella geometrica. Australian Journal of Chemistry, 45, 1705-1743.
6. Funayama S, Eda S, Komiyama K, Ohmura S, Tokunaga T. (1989) Structure of phenazinomycin, a novel antitumor antibiotic. Tetrahedron Letters, 30, 3151-3154.
7. Wu H, Nakamura H, Kobayashi J, Ohizumi Y, Hirata Y. (1984) Agelasine-E and-F, novel monocyclic diterpenoids with 9-methyladeninium unit possessing inhibitory effects on Na, K-ATPase isolated from the Okinawan sea sponge Agelas nakamurai Hoshino. Tetrahedron Letters, 25, 3719-3722.
8. Bakkestuen AK, Gundersen L-L. (2003) Synthesis of (+)-trixagol and its enantiomer, the terpenoid side chain of (-)-agelasine E. Tetrahedron, 59, 115-121.
9. Kinoshita Y, Kitahara T. (1997) Total synthesis of phenazinomycin and its enantiomer via high-pressure reaction. Tetrahedron Letters, 38, 4993-4996.
10. Bakkestuen AK, Gundersen L-L, Petersen D, Utenova BT, Vik A. (2005) Synthesis and antimycobacterial activity of agelasine E and analogs. Organic & Biomolecular Chemistry, 3, 1025-1033.
11. Schulte-Elte K. Muller BL, Ohloff G. (1978) Photosensitized oxygenation of (E)-and (Z)-(+)-γ-monocyclofarnesol. An access to (S)-(+)-ambra- aldehyde. Nouveau Journal de Chimie, 2, 427-430.
12. Barrero AF, Alvarez-Manzaneda EJ, Chahboun R, Cuerva JM, Segovia A. (2000) Synthetic applications of the thermal rearrangement of ozonides: First enantiospecific synthesis of marine metabolite Luffarin W. Synlett, 1269-1272.
13. Serra S, Fuganti C, Brenna E. (2006) Synthesis, olfactory evaluation, and determination of the absolute configuration of the 3, 4-didehydroionone stereoisomers. Helvetica Chimica Acta, 89, 1110-1122.
14. Fuganti C, Serra S, Zenoni A. (2000) Synthesis and olfactory evaluation of (+)-and (-)-gamma-ionone. Helvetica Chimica Acta, 83, 2761-2768.