（+）-黑蚁素215B的可逆二聚化
Reversible dimerization of (+)-myrmicarin 215B.
作者信息
Ondrus Alison E, Movassaghi Mohammad
机构信息
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA.
出版信息
Org Lett. 2009 Jul 16;11(14):2960-3. doi: 10.1021/ol9008552.
Brønsted acid promoted reversible dimerization of myrmicarin 215B leads to formation of a new heptacyclic product, isomyrmicarin 430B, that possesses a C1,C2-trans,C2,C3-trans-substituted cyclopentane ring. Mechanistic studies illustrate that isomyrmicarin 430B arises by isomerization of isomyrmicarin 430A via fragmentation to tricyclic azafulvenium ions. Factors influencing the structure of heptacyclic isomyrmicarin products and potential relevance of this reversible vinyl pyrroloindolizine dimerization to the biosynthesis of complex myrmicarins are discussed.
布朗斯台德酸促进了蚁巢菌素215B的可逆二聚反应，形成了一种新的七环产物——异蚁巢菌素430B，它具有一个C1、C2-反式、C2、C3-反式取代的环戊烷环。机理研究表明，异蚁巢菌素430B是由异蚁巢菌素430A通过碎片化形成三环氮杂富烯离子异构化而来。讨论了影响七环异蚁巢菌素产物结构的因素以及这种可逆的乙烯基吡咯并吲哚嗪二聚反应与复杂蚁巢菌素生物合成的潜在相关性。
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