Jiang Lei, Martinelli Joseph R, Burke Steven D
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1396, USA.
J Org Chem. 2003 Feb 7;68(3):1150-3. doi: 10.1021/jo026302w.
C(2)-symmetric dihydroxycyclohexene 1 was desymmetrized via a one-pot Criegee ozonolysis/acylation protocol to afford acetal-lactone 2. Installation of the allyl side chain on the convex face of the bicyclic system and subsequent reduction provided the desired tetrahydrofuran 4 with the correct relative and absolute stereochemistries. Simple functional group manipulations led to the desired F-ring module 3 of halichondrin B.
通过一锅法Criegee臭氧分解/酰化反应使C(2)对称的二羟基环己烯1去对称化，得到缩醛内酯2。在双环体系的凸面上安装烯丙基侧链并随后进行还原，得到具有正确相对和绝对立体化学的所需四氢呋喃4。简单的官能团操作得到了所需的海兔毒素B的F环模块3。
