Total Synthesis of Tricolorin A.
Tricolorin A (1), a structurally amazing resin glycoside with promising bioactivities from Ipomoea tricolor cav. (convolvulaceae), was synthesized in a total of 45 steps, with the longest linear sequence of 20 steps and overall yield of 0.65% from D-mannitol. The AB disaccharide 19-membered lactone 2 was constructured by a regioselective macrolactonization using Corey-Nicolaou protocol. The macrolactone tetrasaccharide 33 was realized either by "one-pot two-step" glycosylation procedure or by a stepwise assembly employing the "armed-disarmed" glycosylation strategy.
Lu
Shou-Fu
SF
State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, China.
O'yang
QinQin
Q
Guo
Zhong-Wu
ZW
Yu
Biao
B
Hui
Yong-Zheng
YZ