Enantiospecific approach to AB-ring system of the diterpenes fusicoccanes

Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

Volumn 50, Issue 1, 2011, Pages 73-76

  Srikrishna, A ^a   Nagaraju, Gopalasetty ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Bicyclo 6.3.0 undecanes; Fusicoccanes; Limonene; Ophiobolins; RCM reaction

Indexed keywords

EID: 79551591904     PISSN: 03764699     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. (a) Mehta G & Singh V, Chem Rev, 99, 1999, 881;
2. (b) Petasis N A & Patane M A, Tetrahedron, 48, 1992, 5757.
3. Muromtsev G S, Voblikova V D, Kobrina N S, Koreneva V M, Krasnopolskaya & Sadovskaya, J Plant Growth Regul, 13, 1994, 39;
4. (a) Ballio A, Chain E B, Leo P D, Erlanger B F, Mauri M & Tonolo A, Nature, 4942, 1964, 297;
5. (b) Barrow K D, Barton D H R, Chain S R, Ohnsorge U F W & Thomas R, J Chem Soc (C), 1971, 1265;
6. (c) For recent report on the isolation of fusicoccanes, see: Komala I, Ito T, Nagashima F, Yagi Y, Kawahata M, Yamaguchi K & Asakawa Y, Phytochemistry, 71, 2010, 1387.
7. (a) Michalak K, Michalak M & Wicha J, Tetrahedron Lett, 46, 2005, 1149;
8. (b) Dake G R, Fenster E E & Patrick B O, J Org Chem, 73, 2008, 6711;
9. (c) For the earlier synthetic approaches including total synthesis of fusicoccanes, see the references cited in 4b.
10. (a) Srikrishna A & Babu N C, Tetrahedron Lett, 42, 2001, 4913;
11. (b) Srikrishna A, Babu N C & Dethe D H, Indian J Chem, 42 B, 2003, 1688;
12. (c) Srikrishna A & Dethe D H, Org Lett, 5, 2003, 2295;
13. (d) Srikrishna A, Babu N C & Rao M S, Tetrahedron, 60, 2004, 2125;
14. (e) Srikrishna A, Pardeshi V H & Satyanarayana G, Tetrahedron: Asymmetry, 21, 2010, 746;
15. (f) Srikrishna A & Pardeshi V H, Tetrahedron, 66, 2010, 8160.
16. (a) Grubbs R H & Chang S, Tetrahedron, 54, 1998, 4413;
17. (b) Fürstner A, Angew Chem Int Ed (Engl), 39, 2000, 3013;
18. (c) Trnka T M & Grubbs R H, Acc Chem Res, 34, 2001, 18;
19. (d) Grubbs R H, Handbook of Metathesis, Vol. 2 (Wiley-VCH), 2003.
20. Mehta G, Krishnamurthy N & Karra S R, J Am Chem Soc, 113, 1991, 5765.
21. Johnson W S, Werthemann L, Bartlett W R, Brocksom T J, Li T-T, Faulkner D J & Petersen R, J Am Chem Soc, 92, 1970, 741.
22. In addition varying amount (10-20%) of easily separable another isomer of the diol 11, perhaps epimeric at the tertiary alcohol, was also obtained.