Total synthesis of 1-oxomiltirone via Suzuki coupling

doi:10.1007/s13659-013-0034-7

Natural Products and Bioprospecting

2013, Vol. 3

Issue (3) : 117-120 DOI: 10.1007/s13659-013-0034-7

Short Communication

Total synthesis of 1-oxomiltirone via Suzuki coupling

Chun-Miao LI^a,c, Hui-Chun GENG^a,b, Ming-Ming LI^a, Gang XU^a, Tie-Jun LING^c, Hong-Bo QIN^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China;
c Key Laboratory of Tea Biochemistry and Biotechnology of Ministry of Education & Ministry of Agriculture, Anhui Agricultural University, Hefei 230036, China

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Abstract Abietane diterpenes and miltirone series have shown important activities and for medical purposes in order to achieve the total synthesis of 1-oxomiltrone 1 and miltirone 4, a versatile intermediate 6 was found. The compound 6 could be used as a precursor A-B-C rings with different oxidative degrees in selected abietane diterpenes when synthesized through high yield Suzuki reaction and subsequent cyclization, and total synthesis of 1-oxomiltirone (1) has been achieved.

Keywords total synthesis Suzuki coupling 1-oxomiltirone abietane diterpenes versatile intermediate

Issue Date: 11 February 2018

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	Gang XU
	Tie-Jun LING
	Hong-Bo QIN

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Chun-Miao LI,Hui-Chun GENG,Ming-Ming LI, et al. Total synthesis of 1-oxomiltirone via Suzuki coupling[J]. Natural Products and Bioprospecting, 2013, 3(3): 117-120.

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http://npb.kib.ac.cn/EN/10.1007/s13659-013-0034-7 OR http://npb.kib.ac.cn/EN/Y2013/V3/I3/117

[1]	(a) Huang, W. G.; Jiang, Y. Y.; Li, Q.; Li, J.; Li, J. Y.; Lu, W.; Cai, J. C. Tetrahedron 2005, 61, 1863-1870; (b) Sairafianpour, M.; Christensen, J.; Stærk, D.; Budnik, B. A.; Kharazmi, A. J. Nat. Prod. 2001, 64, 1398-1403.
[2]	Kobayashi, K.; Nishino, C. Agric. Biol. Chem. 1986, 50, 2405-2407.
[3]	(a) Ghosal, M.; Karpha, K.; Manuka, T. K.; Mukherjee, D. Indian J. Chem. B Org. 1992, 31, 524-525; (b) Gupta, P. D.; Pal, A.; Mukherjee, D. Indian J. Chem. B Org. 2001, 40, 1033-1035.
[4]	Huang, W. G.; Li, Y. F.; Lu, W.; Aisa, H. A. Chem. Nat. Compd. 2006, 42, 665-667.
[5]	Majetich, G.; Liu, S.; Fang, J.; Siesel, D.; Zhang, Y. J. Org. Chem. 1997, 62, 6928-6951.
[6]	Ghosal, M.; Sukanta Bhattacharyya, S.; Mukherjee, D. Tetrahedron Lett. 1989, 30, 3469-3470.
[7]	Yadav, J. S.; Kondaji, G.; Shiva Ram Reddy, M.; Srihari, P. Tetrahedron Lett. 2008, 49, 3810-3813.
[8]	Ruel, F. S.; Braun, M. P.; Johnson, C. R. Org. Synth. 2004, Coll. Vol. 10, 467-470.
[9]	Sairafianpour, M.; Christensen, J.; Stærk, D.; Budnik, A. B.; Kharazmi, A.; Bagherzadeh, K.; Jaroszewski, W. J. J. Nat. Prod. 2001, 64, 1398-1401.

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