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Synlett

Volumn , Issue 14, 2008, Pages 2101-2102

Synthesis of ptaeroxylin (desoxykarenin): An unusual chromone from the sneezewood tree Ptaeroxylon obliquum

(3) Muscarella, Marina a,b Kimber, Marc C a Moody, Christopher J a

a UNIVERSITY OF NOTTINGHAM (United Kingdom)

b UNIVERSITY OF PALERMO (Italy)

Author keywords

Chromones; Claisen rearrangement; Natural products; Ring closing metathesis reaction

Indexed keywords

CHROMONE DERIVATIVE; DESOXYKARENIN; NATURAL PRODUCT; OXEPINOCHROME PTAEROXYLIN; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CLAISEN REARRANGEMENT; DRUG ISOLATION; DRUG STRUCTURE; INFRARED SPECTROSCOPY; RING CLOSING METATHESIS; TREE; ULTRAVIOLET SPECTROSCOPY;

EID: 51149095789 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078250 Document Type: Article

Times cited : (10)

References (11)

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2
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3
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4
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5
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- Rehder, K. S.; Kepler, J. A. Synth. Commun. 1996, 26, 4005.
- (1996) Synth. Commun , vol.26 , pp. 4005
- Rehder, K.S.¹ Kepler, J.A.²

6
- 51149103127
- Synthesis of 6-Allyl-5,7-dihydroxy-2-methyl-4H-chromen-4-one (11) 5-Allyloxy-7-hydroxy-2-methyl-4H-chromen-4- one (8, 0.15 g, 0.65 mmol) was heated in N,N-dimethylaniline (1.5 mL) and Ac2O (1.5 mL) at 200°C for 1.5 h in a microwave reactor (300 W, The mixture was poured into HCl (6 M, 40 mL) and then extracted with EtOAc (3 x 30 mL, Chromatography (CH2Cl2-EtOAc, 95:5) gave a mixture of 6-allyl-5-hydroxy-2-methyl-4-oxo-4H-chromen-7-yl acetate (9, 0.06 g, 34, and 6-allyl-2-methyl-4-oxo-4H-chromene-5,7-yl diacetate (10, 0.12 g, 58, To the above mixture (0.13 g) was added a solution of K2CO3 (0.15 g) in MeOH (2.5 mL, The solution was heated under reflux for 30 min. The solvent was removed in vacuo and H 2O (10 mL) was added. The solution was then acidified with HCl (6 M) and the resulting solid filtered to give the title compound 11 as a colour
- 2), 20.3 (Me).

7
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- (a) Stefinovic, M.; Snieckus, V. J. Org. Chem. 1998, 63, 2808.
- (1998) J. Org. Chem , vol.63 , pp. 2808
- Stefinovic, M.¹ Snieckus, V.²

8
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- (b) Chattopadhyay, S. K.; Dey, R.; Biswas, S. Synthesis 2005, 403.
- (2005) Synthesis , pp. 403
- Chattopadhyay, S.K.¹ Dey, R.² Biswas, S.³

9
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- (c) Rotzoll, S.; Görls, H.; Langer, P. Synthesis 2008, 45.
- (2008) Synthesis , pp. 45
- Rotzoll, S.¹ Görls, H.² Langer, P.³

10
- 51149112557
- Synthesis of 5-Hydroxy-6,9-dihydro-2,8-dimethyl-4H-oxepino[3,2-g]chromen-4-one (Ptaeroxylin, 2) A solution of 6-allyl-5-hydroxy-2-methyl-7, 2-methylprop-2-en-1-yl)oxy]-4 H-chromen-4-one (12, 0.035 g, 0.135 mmol) in CH2Cl 2 (65 mL, 0.002M) was treated with a single portion (0.021 g, 20 mol, of bis(tricyclohexylphosphine)benzylideneruthenium(IV) dichloride. The solution was heated under reflux for 18 h. The solvent was removed in vacuo and the brown residue filtered through a short pad of Celite using cyclohexane-EtOAc (9:1) as eluent. The solvent was then removed and the residue purified by chromatography (cyclohexane-EtOAc, 9:1) to give the title compound 2 as a colourless solid 0.020g, 64, for analytical data, see ref. 9
- 2 (65 mL, 0.002M) was treated with a single portion (0.021 g, 20 mol%) of bis(tricyclohexylphosphine)benzylideneruthenium(IV) dichloride. The solution was heated under reflux for 18 h. The solvent was removed in vacuo and the brown residue filtered through a short pad of Celite using cyclohexane-EtOAc (9:1) as eluent. The solvent was then removed and the residue purified by chromatography (cyclohexane-EtOAc, 9:1) to give the title compound 2 as a colourless solid (0.020g, 64%); for analytical data, see ref. 9.

11
- 51149120822
- Table 1 Comparison of Data for Natural and Synthetic Ptaeroxylin
- Table 1 Comparison of Data for Natural and Synthetic Ptaeroxylin

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.