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. Author manuscript; available in PMC: 2013 Nov 18.
Published in final edited form as: Tetrahedron. 2012 Nov 18;68(46):9307–9343. doi: 10.1016/j.tet.2011.12.070

Table 2.

Molar rotations of bistramide diastereomers.

Stereogenic segments composing bistramide [M]D
C6–C11 THP/amide C22–C31 Spiroketal C34 ketone
(6S, 9R, 11R, 15S, 16R) [M]D = +119a (22S, 23R, 27R, 31R) [M]D = −156 (34R) [M]D = −51 −88

(34S) [M]D = +51d +14

(22R, 23S, 27S, 31S) [M]D = +156b (34R) [M]D = −51 +224

(34S) [M]D = +51d +326

(6R, 9S, 11S, 15R, 16S) [M]D = −119 (22S, 23R, 27R, 31R) [M]D = −156 (34R) [M]D= −51 −326

(34S) [M]D = +51d −224

(22R, 23S, 27S, 31S) [M]D = +156b (34R) [M]D = −51 −14

(34S) [M]D= +51d +88
a

synthetic

b

derived from synthetic 78.

c

from normanicone (+)-79.