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. Author manuscript; available in PMC: 2015 Jun 25.
Published in final edited form as: J Am Chem Soc. 2002 Feb 27;124(8):1606–1614. doi: 10.1021/ja0105156

Table 3.

Long-Range Couplings Observed in the HMBC Spectra of the New Premithramycin (11, 12) and Mithramycin Derivatives (13, 14) (Most Important Couplings Are Highlighted in Bold)

H-position C-position
11 12 13 14
2 1,3,1′,1C 3,1′,1C
3 4
4 1,4-OCH3,4a,5
α 4a 4a,10
β 2,3,4a,9a,10 2,4a,9a,10
4-OCH3 4 4
4a
5 6,7,8,8a,9,9a,10 6,7,10
α 4a,5a
β
6 5,6a,7,10a,11a 5,7,11a
7 6,8,9,10a 6,8,9,10a
7-CH3 5,6,7,8,8a,9a 6,7,8,10a
9 7,8,10,10a
9-CH3 8,9,10
10 4,5,8a,9a,10a 4,5,8,8a,9,9a,10a
14 2,13 13
1′ 2,3,4,1′-OCH3,2′ 3,4,1′-OCH3,2′
1′-OCH3 1′,3′ 2,1′
3′ 2′,4′,5′ 2′
4′ 2′,5′
5′ 2′,3′,4′ 3′,4′
1A 12a 6 6,2A
2Aa 1A,3A 1A,3A 1A,3A 1A,3A
2Ae 3A,4A 3A,4A 1A,3A,4A 1A,3A,4A
3A 1B 1B 2A,4A,1B 1B
4A 3A,5A,6A 3A,5A
5A 1A,6A 1A,6A 1A,3A,4A,6A 1A,4A
6A 4A,5A 4A,5A 4A,5A 5A
1B 3A 3A 3A 3A,2B
2Ba 1B,3B 1B,3B 1B,3B,4B 1B,3B
2Be 1B,3B,4B 1B,3B,4B
3B 2B,4B,5B 4B
4B 5B 5B 3B,5B,6B 3B,5B
5B 4B,6B 4B,6B 1B,3B,4B,6B 1B,3B,4B
6B 5B 5B 3B,4B,5B 2B,5B
1C 2,2C
2Ca 1C,3C 1C,3C
2Ce 1C,3C,4C 1C,3C,4C
3C 2C,1D 4C,1D
4C 3C,5C
5C 1C,3C,4C,6C 1C,4C
6C 4C,5C 2C,4C,5C
1D 3C 3C
2Da 1D,3D 1D,3D
2De 4D
3D 2D,4D
4D 2D,3D,5D 2D,3D
5D 1D,4D,6D 3D,4D
6D 4D,5D
1E 2E
2Ea 1E
2Ee 1E,4E
3E-CH3 1E,2E,3E,4E
5E 1E,4E
6E 4E,5E