Facile enantiospecific synthesis of (+)-iso-cladospolide B

Tetrahedron Asymmetry

Volumn 21, Issue 3, 2010, Pages 275-276

  Prasad, Kavirayani R ^a   Gandi, Vasudeva Rao ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BUTENOLIDE; CLADOSPOLIDE B; LACTONE DERIVATIVE; TARTARIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CLADOSPORIUM; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; OLEFINATION; PRIORITY JOURNAL; REACTION ANALYSIS; RING CLOSING METATHESIS; WITTIG REACTION;

EID: 77949298120     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.01.011     Document Type: Article

References (28)

1. Cameron J.S., Abbanat D., Bernan V.S., Maiese W.M., Greenstein M., Jompa J., Tahir A., and Ireland C.M. J. Nat. Prod. 63 (2000) 142-145
2. Gesner S., Cohen N., Ilan M., Yarden O., and Carmeli S. J. Nat. Prod. 68 (2005) 1350
3. Sharma G.V.M., Reddy J.J., and Reddy K.L. Tetrahedron Lett. 47 (2006) 6531
4. Sharma G.V.M., Reddy J.J., and Reddy K.L. Tetrahedron Lett. 47 (2006) 6537
5. Ferrié L., Reymond S., Capdevielle P., and Cossy J. Synlett (2007) 2891
6. For other syntheses of the putative structure of iso-cladospolide B see:. Srihari P., Bhasker E.V., Harshavasdhan S.J., and Yadav J.S. Synthesis (2006) 4041
7. Pandey S.K., and Kumar P. Tetrahedron Lett. 46 (2005) 6625
8. Franck X., Vaz Araujo M.E., Jullian J.-C., Hocquemiller R., and Figadere B. Tetrahedron Lett. 42 (2001) 2801
9. Prasad K.R., and Gandi V.R. Synlett (2009) 2593
10. Prasad K.R., and Swain B. Tetrahedron: Asymmetry 19 (2008) 1134
11. Prasad K.R., and Gholap S.L. J. Org. Chem. 73 (2008) 2
12. Prasad K.R., and Gholap S.L. J. Org. Chem. 73 (2008) 2916
13. Prasad K.R., and Gandi V. Tetrahedron: Asymmetry 19 (2008) 2616
14. Prasad K.R., and Chandrakumar A. J. Org. Chem. 72 (2007) 6312
15. Prasad K.R., and Dhaware M.G. Synthesis (2007) 3697
16. Prasad K.R., and Dhaware M.G. Synlett (2007) 1112
17. Prasad K.R., Penchalaiah K., Choudhary A., and Anbarasan P. Tetrahedron Lett. 48 (2007) 309
18. Prasad K.R., and Chandrakumar A. Tetrahedron 63 (2007) 1798
19. Prasad K.R., and Anbarasan P. Tetrahedron: Asymmetry 17 (2006) 1146
20. Prasad K.R., and Anbarasan P. Tetrahedron 62 (2006) 8303
21. Prasad K.R., and Anbarasan P. Tetrahedron: Asymmetry 17 (2006) 850
22. Prasad K.R., and Gholap S.L. J. Org. Chem. 71 (2006) 3643
23. Prasad K.R., and Gholap S.L. Synlett (2005) 2260
24. Prasad K.R., and Anbarasan P. Synlett (2006) 2087
25. Takahashi S., Ogawa N., Koshino H., and Nakata T. Org. Lett. 7 (2005) 2783
26. The formation of a minor amount of the dimer resulting from the dimerization of 7 is also observed. No efforts were made to determine the E/Z ratio of the olefin in 8. However, the stereochemistry of the olefin is of no consequence as it is saturated in the next step by hydrogenation.
27. Purification of the silyl ether by column chromatography always resulted in contamination with traces of an unidentified silyl impurity.
28. 1H NMR. [For Z-predominant Wittig olefinations with glyceraldehyde acetonide see: Minami, N.; Ko, S, S.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 1109]. For a review on Wittig olefination reactions see: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.