Table 1. Yield of Each Compound in the Steps of Schemes 1 and 2.
compd. | 4 (%) | 5 (%) | 6 (%) | 8 (%) | 2 (%) | 9 (%) | 1 (%) |
---|---|---|---|---|---|---|---|
a | 33 | 79 | 99 | 56 | 52 | 53 | 72 |
b | 73 | 95 | 25 | 63 | 96a | 35 | 35 |
c | 98 | 88 | 68 | 21 | 19 | 37 | 67 |
d | 95 | 87 | 57 | 30 | 45 | 26b | 78 |
e | 47 | 62 | 68 | 21 | 13 |
All-E configuration was deteriorated after deprotection (all-E:Z = 1.7:1).
The reaction was performed by one-pot double olefination between C20 diphosphonate 10 and 4d (2 equiv).