Enantioselective first total syntheses of 2-(formylamino)trachyopsane and ent-2-(isocyano)trachyopsane via a biomimetic approach

Synlett

Volumn , Issue 1, 2009, Pages 32-34

  Srikrishna, A ^a   Ravi, G ^a   Venkata Subbaiah, D R C ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Acid catalysed rearrangement; Biomimetic synthesis; Enantioselective synthesis; Marine sesquiterpenes; Natural products

Indexed keywords

EID: 62349124195     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087382     Document Type: Article

References (10)

1. Patil, A. D.; Freyer, A. J.; Reichwein, R.; Bean, M. F.; Faucette, L.; Johnson, R. K.; Haltiwanger, R. C.; Eggleston, D. S. J. Nat. Prod. 1997, 60, 507.
2. (a) He, H. Y.; Faulkner, D. J.; Shumsky, J. S.; Hong, K.; Clardy, J. J. Org. Chem. 1989, 54, 2511.
3. (b) He, H. Y.; Salvi, J.; Catalos, R. F.; Faulkner, D. J. J. Org. Chem. 1992, 57, 3191.
4. Okino, T.; Yoshimura, E.; Hirota, H.; Fusetani, N. Tetrahedron 1996, 52, 9447.
5. Karuso, P.; Poiner, A.; Scheuer, P. J. J. Org. Chem. 1989, 54, 2095.
6. Fusetani, N.; Wolstenhohne, H. J.; Matsunaga, S.; Hirota, H. Tetrahedron Lett. 1991, 32, 7291.
7. So far there is no report in the literature on the total synthesis or model studies of any racemic or optically active trachyopsanes.
8. Srikrishna, A.; Gharpure, S. J. Chem. Commun. 1998, 1589.
9. 4; in all these experiments either starting material recovered or a complex mixture was produced. Reaction with formic acid generated the formate ester of the alcohol 17, whereas PTSA (1 equiv) in MeCN produced a mixture of the acetate and tosylates of the alcohol 17 along with the rearranged product 18. Significant amount (50-60%) of rearranged product 18 was formed when the reaction was carried out with PTSA (1 equiv) in refluxing benzene.
10. Chen, H. G.; Goel, O. P.; Kesten, S.; Knobelsdorf, J. Tetrahedron Lett. 1996, 37, 8129.