Total synthesis of the microtubule-stabilizing agent (-)-laulimalide

被引：102

作者：

Paterson, I ^{[1
]}

De Savi, C ^{[1
]}

Tudge, M ^{[1
]}

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 20期

关键词：

D O I：

10.1021/ol010150u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The total synthesis of the potent microtubule-stabilizing anticancer agent (-)-laulimalide has been achieved in 27 steps and 2.9% overall yield. Notable features are the use of Jacobsen HDA chemistry for the enantioselective construction of the side chain dihydropyran, a diastereoselective aldol coupling using chiral boron enolate methodology, a Mitsunobu macrolactonization, and a Sharpless AE to introduce the epoxide onto des-epoxy-laulimalide.

引用

页码：3149 / 3152

页数：4

共 35 条

[1]

[Anonymous], CATALYTIC ASYMMETRIC

[2]

BOLLAG DM, 1995, CANCER RES, V55, P2325

[3] LAULIMALIDES - NEW POTENT CYTO-TOXIC MACROLIDES FROM A MARINE SPONGE AND A NUDIBRANCH PREDATOR [J].