A novel synthesis of 5-hydroxy-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one

被引：19

作者：

Fox, ME

Lennon, IC

Meek, G

机构：

[1] Chirotech Technol Ltd, Cambridge CB4 0WG, England

[2] Sarawak MediChem Inc, Woodridge, IL USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 16期

关键词：

selective desulfonation; chromene synthesis; calanolide A;

D O I：

10.1016/S0040-4039(02)00428-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of 5-hydroxy-2.2-dimethyl-10-propyl-2H-pyrano[2.3-f]chromen-8-one utilising a novel selective desulfonylation protocol is described. This method provides facile access to a key intermediate for the asymmetric synthesis of calanolide A. (C), 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：2899 / 2902

页数：4

相关论文

共 17 条

[1] RESOLUTION AND COMPARATIVE ANTI-HIV EVALUATION OF THE ENANTIOMERS OF CALANOLIDE-A AND CALANOLIDE-B [J].

CARDELLINA, JH ;

BOKESCH, HR ;

MCKEE, TC ;

BOYD, MR .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (09) :1011-1014

[2] TOTAL SYNTHESIS OF (PLUS-OR-MINUS)-CALANOLIDE-A, A NON-NUCLEOSIDE INHIBITOR OF HIV-1 REVERSE-TRANSCRIPTASE [J].

CHENERA, B ;

WEST, ML ;

FINKELSTEIN, JA ;

DREYER, GB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (21) :5605-5606

[3]

Desai R D, 1956, J INDIAN CHEM SOC, V33, P661

[4] SYNTHESIS OF OPTICALLY-ACTIVE CALANOLIDE-A AND CALANOLIDE-B [J].

DESHPANDE, PP ;

TAGLIAFERRI, F ;

VICTORY, SF ;

YAN, SJ ;

BAKER, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :2964-2965

[5] Synthesis, chromatographic resolution, and anti-human immunodeficiency virus activity of (+/-)-calanolide A and its enantiomers [J].

Flavin, MT ;

Rizzo, JD ;

Khilevich, A ;

Kucherenko, A ;

Sheinkman, AK ;

Vilaychack, V ;

Lin, L ;

Chen, W ;

Greenwood, EM ;

Pengsuparp, T ;

Pezzuto, JM ;

Hughes, SH ;

Flavin, TM ;

Cibulski, M ;

Boulanger, WA ;

Shone, RL ;

Xu, ZQ .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (06) :1303-1313

[6]

FOX ME, 2001, Patent No. 6313320

[7] HIV-inhibitory natural products .30. Structure-activity modifications of the HIV-1 inhibitors (+)-calanolide A and (-)-calanolide B [J].

Galinis, DL ;

Fuller, RW ;

McKee, TC ;

Cardellina, JH ;

Gulakowski, RJ ;

McMahon, JB ;

Boyd, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (22) :4507-4510

[8]

GAMES DE, 1971, CHEM COMMUN, P1005

[9]

GREENE TW, 1991, PROTECTIVE GROUPS OR, P168

[10] Synthesis of (+)-calanolide A, an anti-HIV agent, via enzyme-catalyzed resolution of the aldol products [J].

Khilevich, A ;

Mar, A ;

Flavin, MT ;

Rizzo, JD ;

Lin, L ;

Dzekhtser, S ;

Brankovic, D ;

Zhang, HP ;

Chen, W ;

Liao, SY ;

Zembower, DE ;

Xu, ZQ .

TETRAHEDRON-ASYMMETRY, 1996, 7 (11) :3315-3326