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. Author manuscript; available in PMC: 2008 Jan 1.
Published in final edited form as: Bioorg Med Chem. 2006 Oct 10;15(1):495–510. doi: 10.1016/j.bmc.2006.09.039

Table 1.

Synthesis and Structures of Lavendamycins

graphic file with name nihms14804f9.jpg

No. R1 R2 R3 R4 % yield hrs (°C )a
19 CH3CO CO2C2H5 H H 55 3 (25-reflux), 19 (reflux)
20 CH3CO CO2CH(CH2)5 H H 59 3 (25-reflux), 1(reflux)
21 CH3CO CO2C5H11-i CH3 H 59 3 (<140), 1 (140)
22 CH3CO CO2(CH2)2N(CH3)2 H H 20 27 (100)
23 CH3CO CO2(CH2)2N(CH3)2 CH3 H 36 5.5 (100)
24 CH3CO CO2C4H9-n H OCH3 66 6 (70-90)
25 CH3CO CO2C4H9-n H F 51 5 (25–150)
26 ClCH2CO CO2CH3 CH3 H 46 3 (25–135), 16 (135)
27 ClCH2CO CO2C4H9-n H H 20 3 (76), 5.75 (76)
28 ClCH2CO CO2C8H17-n H H 53 6 25–100), 5.5 (100)
29 n-C3H7CO CO2CH3 H H 59 3 (25–130), 22 (130)
30 n-C3H7CO CO2CH3 CH3 H 44 3 (25–130), 16 (130)
31 n-C3H7CO CO2C5H11-i H H 70 4 (25-reflux), 17 (reflux)
32 n-C3H7CO CO2C8H17-n H H 80 5 (25–85), 16 (85)
33 i-C3H7CO CO2CH3 H H 63 3 (25–130), 4 (130)
34 i-C3H7CO CO2C4H9-n H H 65 5(25-125), 3 (125)
a

The reaction solvent used for producing 22-25, 27 and 29 was dry anisole and for the remainder dry xylene was used.