Synthesis of the Ring C Pyrrole of Native Chlorophylls and Bacteriochlorophylls
Synthesis of the Ring C Pyrrole of Native Chlorophylls and Bacteriochlorophylls
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天然叶绿素和细菌叶绿素的C环吡咯的合成
DOI：
10.1021/acs.joc.9b01650
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发表时间：
2019
期刊：
影响因子：
--
通讯作者：
Lindsey, Jonathan S.
中科院分区：
文献类型：
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作者：
Wang, Pengzhi;Chau Nguyen, Khiem;Lindsey, Jonathan S.
作为开发（细菌）叶绿素家族成员的实际合成计划的一部分，已经开发了2-碘-3-甲基-4-（3-甲氧基-1,3-二氧丙基）吡咯（通用环C的前体）的两条路线。C环的β-酮酯经Knoevenagel缩合和与D环组分的Nazarov环合，可得到E环，如模拟合成所示。从n - tips -吡咯或4-氧-2-戊烯和TosMIC开始，开发了两条可行的路线，可以提供数克数量的这种表面上简单的吡咯。
As part of a program to develop practical syntheses of members of the family of (bacterio)chlorophylls, two routes to 2-iodo-3-methyl-4-(3-methoxy-1,3-dioxopropyl)pyrrole, a precursor of the universal ring C, have been developed. The β-ketoester of ring C is expected to give rise to ring E upon Knoevenagel condensation and Nazarov cyclization with a ring D constituent as demonstrated in an analogue synthesis. Two viable routes were developed beginning withN-TIPS-pyrrole or with 4-oxo-2-pentene and TosMIC, affording multi-gram-quantities of this ostensibly simple pyrrole.