MACROCYCLIZATION THROUGH RADICAL-MEDIATED VINYLCYCLOPROPANE ALKENE CONDENSATION - FACILE ENTRY INTO THE BREFELDIN RING-SYSTEM
MACROCYCLIZATION THROUGH RADICAL-MEDIATED VINYLCYCLOPROPANE ALKENE CONDENSATION - FACILE ENTRY INTO THE BREFELDIN RING-SYSTEM
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DOI：
10.1021/jo00076a056
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发表时间：
1993-11-19
影响因子：
3.6
通讯作者：
PARVEZ, M
中科院分区：
文献类型：
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作者：
FELDMAN, KS;BERVEN, HM;PARVEZ, M
通过用催化量的苯硫基处理带有ω-烯烃单元的官能化乙烯基环丙烷，制备了具有与核心乙烯基环戊烷单元稠合的11元环的双环产物。这种自由基介导的乙烯基环丙烷/烯烃环化缩合的分子内延伸仅以适度的非对映选择性进行。反应产物类似于天然存在的抗生素的布雷菲德菌素家族的成员。
Bicyclic products featuring an 11-membered ring fused to a core vinylcyclopentane unit are produced upon treatment of functionalized vinylcyclopropanes bearing an omega-alkene unit with a catalytic amount of phenylthio radical. This intramolecular extension of a radical-mediated vinylcyclopropane/alkene cyclocondensation proceeds with only modest diastereoselectivity. The reaction products resemble members of the brefeldin family of naturally occurring antibiotics.