Skip to main content
. Author manuscript; available in PMC: 2008 Jun 25.
Published in final edited form as: Tetrahedron. 2007 Jun 25;63(26):5768–5796. doi: 10.1016/j.tet.2007.02.058

Table 2. Assessment of C2 stereochemistry of 36, 9, 10, 76, and 39.

graphic file with name nihms25213f25.jpg

entry starting material steps overall yield product [(+)- or (−)-75]
graphic file with name nihms25213t2.jpg 1) LAH
1 2) TBSCl, Imidazole 76% (+)-(R)-75
graphic file with name nihms25213t3.jpg 1) BH3·SMe2, THF
2 2) TBSCl, Imidazole 84% (+)-(R)-75
3) CAN
graphic file with name nihms25213t4.jpg 1) BH3·SMe2, THF
3 2) TBSCl, Imidazole 68% (+)-(R)-75
3) CAN
graphic file with name nihms25213t5.jpg 1) DIBAL, −78 °C
4 2) TBSCl, Imidazole 56% (+)-(R)-75
3) CAN
graphic file with name nihms25213t6.jpg 1) DIBAL, −78 °C
5 2) TBSCl, Imidazole 61% (−)-(S)-75
3) CAN