Total synthesis of microcarpalide

Tetrahedron Letters

Volumn 44, Issue 14, 2003, Pages 2873-2875

  Gurjar, Mukund K ^a   Nagaprasad, Ravi ^a   Ramana, C V ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALCOHOL; ALKENOIC ACID; ESTER DERIVATIVE; LACTONE DERIVATIVE; MANNOSE; MICROCARPALIDE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DEPROTECTION REACTION; DIHYDROXYLATION; ISOMER; PRECURSOR; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0037474667     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00441-6     Document Type: Article

References (18)

1. Ratnayake A.S., Yoshida W.Y., Mooberry S.L., Hemscheidt T. Org. Lett. 3:2001;3479-3481.
2. Fürstner A., Radkowski K. Chem. Commun. 2001;671-672.
3. Fürstner A., Radkowski K., Wirtz C., Goddard R., Lehmann C.W., Mynott R. J. Am. Chem. Soc. 124:2002;7061-7069.
4. During our work in progress, Marco and co-workers reported the first total synthesis of microcarpalide using RCM as the key transformation. See: Murga J., Falmoir E., Garcia-Fortanet J., Carda M., Marco J.A. Org. Lett. 4:2002;3447-3449.
5. Sharpless K.B., Amberg W., Bennani Y.L., Crispino G.A., Hartung J., Jeong K.-S., Kwong H.-L., Morikawa K., Wang Z.-M., Xu D., Zhang X.-L. J. Org. Chem. 57:1992;2768-2771.
6. Kolb H.C., VanNieuwenhze M.S., Sharpless K.B. Chem. Rev. 94:1994;2483-2547.
7. Hanack M., Kunzmann E., Schumacher W. Synthesis. 1978;26.
8. 4: C, 65.66; H, 11.02. Found: C, 65.07; H, 10.83.
9. Moore B.S., Cho H., Casati R., Kennedy E., Reynolds K.A., Mocek U., Beale J.M., Floss H.G. J. Am. Chem. Soc. 115:1993;5254-5266.
10. Coutrot P., Grison C., Lecouvey M. Bull. Soc. Chim. Fr. 134:1997;27-46.
11. Smith A.B. III, Qiu Y., Jones D.R., Kobayashi K. J. Am. Chem. Soc. 117:1995;12011-12012.
12. Rama Rao A.V., Reddy E.R., Joshi B.V., Yadav J.S. Tetrahedron Lett. 28:1987;6497-6500.
13. Monti H., Leandri G., Klos-Ringuet M., Corriol C. Synth. Commun. 13:1983;1021-1026.
14. Dalcanale E., Montanari F. J. Org. Chem. 51:1986;567-569.
15. 4: C, 74.09; H, 7.11. Found: C, 74.16; H, 7.49.
16. Corey E.J., Gras J.L., Ulrich P. Tetrahedron Lett. 11:1976;809-812.
17. Bhatt M.V., Kulkarni S.V. Synthesis. 1983;249-334.
18. 7: C, 71.80; H, 8.51. Found: C, 71.97; H, 8.98.