Determination of the absolute configuration of Anisotome irregular diterpenes: Application of CD and NMR methods

Chirality

Volumn 16, Issue 8, 2004, Pages 549-558

  Van Klink, John W ^a   Baek, Seung Hwa ^b   Barlow, Anna J ^a,d   Ishii, Hideki ^c   Nakanishi, Koji ^c   Berova, Nina ^c   Perry, Nigel B ^a   Weavers, Rex T ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b Wonkwang University   (South Korea)

^c Och Spine at New York Presbyterian Hospitals   (United States)

^d UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

Circular dichroism; Exciton chirality; Irregular diterpene; NMR; PGME; Phenylglycine methyl ester; Porphyrin tweezer; Synthesis

Indexed keywords

ANISOTOMENAL; ANISOTOMENOIC ACID; ANISOTOMENOL; CARBOXYLIC ACID; DITERPENE; PHENYLGLYCINE METHYL ESTER; PLANT EXTRACT; PORPHYRIN DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ANISOTOME; ANISOTROPY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; ENANTIOMER; MOLECULAR MODEL; NEW ZEALAND; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

ANGIOSPERMS; CIRCULAR DICHROISM; DITERPENES; GLYCINE; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 4544283936     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.20074     Document Type: Article

References (15)

1. van Klink JW, Barlow AJ, Perry NB, Weavers RT. A new irregular diterpene skeleton from Anisotome flexuosa. Tetrahedron Lett 1999;40: 1409-1412.
2. Zidorn C, Sturm S, Dawson JW, van Klink JW, Stuppner H, Perry NB. Chemosystematic investigations of irregular diterpenes in Anisotome and related New Zealand Apiaceae. Phytochemistry 2002;59:293-304.
3. van Klink JW, Barlow AJ, Benn MH, Perry NB, Weavers RT. Chemistry of New Zealand Apiaceae: new irregular diterpenes from Anisotome flexuosa and A. haastii showing conformational exchange. Aust J Chem 2000;53:939-944.
4. Eliel EL, Wilen SH, Mander LN. Stereochemistry of organic compounds. New York: John Wiley & Sons; 1994. p 101-147.
5. Dunitz JD. X-ray analysis and the structure of organic molecules, 2nd ed. Switzerland: VCHA; 1995. p 129-148.
6. Huang X, Nakanishi K, Berova N. Porphyrins and metalloporhyrins: versatile circular dichroic reporter groups for structural studies. Chirality 2000;12:237-255.
7. Kurtán T, Nesnas N, Li Y-Q, Huang X, Nakanishi K, Berova N. Chiral recognition by CD-sensitive dimeric zinc porphyrin host. 1. Chiroptical protocol for absolute configurational assignments of monoalcohols and primary monoamines. J Am Chem Soc 2001;123:5962-5973.
8. Kurtán T, Nesnas N, Koehn FE, Li Y-Q, Nakanishi K, Berova N. Chiral recognition by CD-sensitive dimeric zinc porphyrin host. 2. Structural studies of host-guest complexes with chiral alcohol and monoamine conjugates. J Am Chem 2001;123:5974-5982.
9. Huang X, Fujioka N, Pescitelli G, Koehn FE, Williamson RT, Nakanishi K, Berova N. Absolute configurational assignments of secondary amines by CD-sensitive dimeric zinc porphyrin host. J Am Chem Soc 2002;124:10320-10335.
10. Proni G, Pescitelli G, Huang X, Quraishi NQ, Nakanishi K, Berova N. Configurational assignment of a-chiral carboxylic acids by complexation to dimeric Zn-porphyrin: host/guest structure, chiral recognition and circular dichroism. J Chem Soc Chem Commun 2002;15: 1590-1591.
11. Proni G, Pescitelli G, Huang X, Nakanishi K, Berova N. Magnesium tetraarylporphyrin tweezer: a sensitive host for recognition of α-chiral carboxylic acids. J Am Chem Soc 2003;125:12914-12927.
12. Seco JM, Quinoa E, Riguera R. The assignment of absolute configuration by NMR. Chem Rev 2004;104:17-118.
13. Yabuuchi T, Kusumi T. Phenylglycine methyl ester, a useful tool for absolute configuration determination of various chiral carboxylic acids. J Org Chem 2000;65:397-404.
14. Specht KM, Nam J, Ho DM, Berova N, Kondru RK, Breatan DN, Wipf P, Pascal RA, Kahne D. Determining absolute configuration in flexible molecules: a case study. J Am Chem Soc 2001;123:8961-8966.
15. Pescitelli G, Gabriel S, Wang Y, Fleischhauer J, Woody RW, Berova N. Theoretical analysis of the porphyrin-porphyrin exciton interaction in circular dichroism spectra of dimeric tetraarylporphyrins. J Am Chem Soc 2003;125:7613-7628.