Microbial Oxidation of Chloroaromatics in the Enantiodivergent Synthesis of Pyrrolizidine Alkaloids: Trihydroxyheliotridanes

Journal of Organic Chemistry

Volumn 55, Issue 15, 1990, Pages 4683-4687

  Hudlicky, Tomas ^a   Luna, Hector ^a   Price, John D ^a   Rulin, Fan ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIZIDINE DERIVATIVE;

ARTICLE; METHODOLOGY; NONHUMAN; REACTION ANALYSIS; SYNTHESIS;

EID: 0024988763     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00302a037     Document Type: Article

References (45)

1. Recipient of the Research Career Development Award, 1984–1989, National Institutes of Health (AI-00564).
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4. For a recent synthesis of crotanecine see: Bennett, R. B. III; Cha, J. K. Abstracts of Papers; 41st Southeast Regional Meeting of the American Chemical Society, Winston-Salem, NC; American Chemical Society: Washington, DC, 1989; Abstract 355. Recent reviews on pyrrolizidine synthesis
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42. A realistic cost estimate for lactols 6a and 6b is $2.40/g from arabinoses, and $1.40/g from chlorobenzene. Labor is comparable for the two processes. The overall yield of lactol 6a from chlorobenzene was 45 %. This compares with a yield of 39% from arabinose.
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45. All nonhydrolytic reactions were carried out in a nitrogen or argon atmosphere, with standard techniques for the exclusion of air and moisture. Glassware used for moisture-sensitive reactions was flame-dried with an internal inert gas sweep. THF, ethyl ether, DME, and benzene were distilled from benzophenone ketyl, dichloromethane, and toluene from calcium hydride. Analytical TLC was performed on silica gel 60F-254 plates. Flash chromatography was performed using Kieselgel 60 (230–400 mesh). Mass spectra were recorded on a DuPont 20–491 or a Varian MAT-112 instrument (low resolution) or on a double-focusing DuPont 21-110C or VGT instrument (exact mass). Infrared spectra were recorded as neat samples (NaCl plates) on a Perkin-Elmer 1600 Series FT spectrometer. Proton NMR spectra were obtained on a Bruker WP-270 instrument. Proton chemical shifts are reported in parts per million (ppm) relative to chloroform (7.24 ppm). Carbon NMR spectra were recorded on a Bruker WP-270 instrument. Carbon chemical shifts are reported in parts per million relative to the center line of the CDC13 triplet (77.0 ppm). The multiplicity is indicated by CH3, CH2, CH, or C and were determined by INEPT experiments.