Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2004(2): 0374-0376
DOI: 10.1055/s-2003-45003
DOI: 10.1055/s-2003-45003
LETTER
© Georg Thieme Verlag Stuttgart · New York
The First Total Synthesis of the Antimicrobial Sesquiterpenes (±)-Enokipodins A and B
Further Information
Received
15 October 2003
Publication Date:
18 December 2003 (online)
Publication History
Publication Date:
18 December 2003 (online)
Abstract
Efficient first total synthesis of antimicrobial sesquiterpenes enokipodins A and B (1 and 2, respectively) and formal total synthesis of cuparene-1,4-diol (5) and cuparene-1,4-quinone (7) have been accomplished starting from 2,5-dimethoxy-4-methylacetophenone employing Claisen rearrangement and ring-closing metathesis reaction as key steps.
Key words
sesquiterpenes - enokipodins A and B - ring-closing metathesis - Claisen rearrangement
- 1
Miles PG.Chang ST. Mushroom Biology: Concise Basics and Current Developments Part III: World Scientific; Singapore: 1997. Chap. 6. p.103-117 -
2a
Ishikawa NK.Yamaji K.Tahara S.Fukushi Y.Takahashi K. Phytochemistry 2000, 54: 777 -
2b
Ishikawa NK.Fukushi Y.Yamaji K.Tahara S.Takahashi K. J. Nat. Prod. 2001, 64: 932 - 3
Toyota M.Koyama H.Asakawa Y. Phytochemistry 1997, 46: 145 - 4
Kajimoto T.Yamashita M.Imamura Y.Takahashi K.Nohara T.Shibata M. Chem. Lett. 1989, 527 - 5
Asakawa Y.Kondo K.Tori M. Phytochemistry 1991, 30: 325 -
6a
Bottom CB.Siehr DJ. Phytochemistry 1975, 14: 1433 -
6b
Bullock J.Darbyshire J. Phytochemistry 1976, 15: 2004 -
6c
Thomson RH. In Naturally Occurring Quinones Academic Press; London: 1971. p.734 -
6d
Natori S.Inouye Y.Nishikawa H. Chem. Pharm. Bull. 1967, 15: 380 -
6e
Natori S.Nishikawa H.Ogawa H. Chem. Pharm. Bull. 1964, 12: 236 - 7
Paul T.Pal A.Gupta PD.Mukherjee D. Tetrahedron Lett. 2003, 44: 737 -
8a
Grubbs RH.Chang S. Tetrahedron 1998, 54: 4413 -
8b
Fürstner A. Angew. Chem., Int. Ed. 2000, 39: 3013 -
8c
Trnka TM.Grubbs RH. Acc. Chem. Res. 2001, 34: 18 - 9
Fuganti C.Serra S. J. Chem. Soc., Perkin Trans. 1 2000, 3758 - 10
McKenzie TC. Org. Prep. Proced. Int. 1987, 435