Total synthesis of (±)-cephalosol via silyl enol ether acylation

Synthesis

Volumn , Issue 6, 2010, Pages 917-922

  Arlt, Alexander ^a   Koert, Ulrich ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Acylation; Cephalosol; Chemoselectivity; Isocoumarins; Lactones

Indexed keywords

ALLYLATIONS; CEPHALOSOL; CHEMO-SELECTIVITY; CHEMOSELECTIVE; ISOCOUMARINS; LACTONE MOIETY; METHYL ACETATES; OXALYL CHLORIDE; RING CLOSURES; SILYL ENOL ETHERS; TOTAL SYNTHESIS;

CHLORINE COMPOUNDS; ETHERS; OLEFINS; ORGANIC COMPOUNDS;

ACYLATION;

ANTIBIOTIC AGENT; CEPHALOSOL; CHLORIDE; ISOCOUMARIN DERIVATIVE; MONOMETHYL OXALYL CHLORIDE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; DRUG SYNTHESIS;

EID: 77749315877     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218647     Document Type: Article

References (16)

1. Zhang H W., Huang W Y., Chen J R., Yan W Z., Xie D Q., Tan R X., Chem. Eur. J. 2008 14 10670
2. Barry R D., Chem. Rev. 1964 64 229, Napolitano E, Org. Prep. Proced. Int. 1997 29 631, Hauser F M., Baghdanov V M., J. Org. Chem. 1988 53 4676, Yao T, Larock R C., J. Org. Chem. 2003 68 5936
3. Babin P, Dunoques J, Tetrahedron Lett. 1984 25 4389
4. Nakamura Y, Ukita T, Org. Lett. 2002 4 2317
5. Johnston H W., Kaslow C E., Langsjuen A, Shriner R L., J. Org. Chem. 1948 13 477
6. Lewis C N., Spargo P L., Staunton J, Synthesis 1986 944
7. Yoshifuji M, Nakamura T, Inamoto N, Tetrahedron Lett. 1987 28 6325
8. Ferguson G, Glidewell C, Acta Crystallogr., Sec. C 2001 57 264
9. Codee J D. C., vandenBos J L., deJong A R., Dinkelaar J, Lodder G, Overkleft H S., vanderMarel G A., J. Org. Chem. 2008 74 38
10. Matovic R, Ivkovic A, Manojlovic M, Tokic-Vujosevic Z, Saicic R N., J. Org. Chem. 2006 71 9411
11. Kim J G., Waltz K M., Garcia I F., Kwiatkowski D, Walsh P J., J. Am. Chem. Soc. 2004 126 12580
12. Knochel P, In Comprehensive Organic Synthesis Vol. 1, Trost B M., Fleming I, Heathcock C H., Pergamon Oxford 1991 211
13. Nakamura M, Hirai A, Sogi M, Nakamura E, J. Am. Chem. Soc. 1998 120 5846
14. Yu W, Mei Y, Kang Y, Hua Z, Org. Lett. 2004 6 3217
15. Bal B S., Childers W E., Pinnick H W., Tetrahedron 1981 37 2091
16. Soorukam D, Qu T, Barrett A G. M., Org. Lett. 2008 10 2833