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2
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引用本文的文献

1
Complete biosynthesis of the bisbenzylisoquinoline alkaloids guattegaumerine and berbamunine in yeast.酵母中双苄基异喹啉生物碱古特加默林和贝巴米宁的全生物合成。
Proc Natl Acad Sci U S A. 2021 Dec 21;118(51). doi: 10.1073/pnas.2112520118.

本文引用的文献

1
[Guattegaumerine, New Bisbenzylisoquinoline Alkaloid from Guatteria gaumeri.].[瓜特加美灵，一种来自高氏瓜馥木的新型双苄基异喹啉生物碱。]
Planta Med. 1983 Sep;49(9):25-7. doi: 10.1055/s-2007-969803.
2
[Syntheses of dl-7,4'-O,O-dibenzyl-3'-bromo-N-methylcoclaurine and its optical resolution. (Studies on the syntheses of heterocyclic compounds. 153.)].
Yakugaku Zasshi. 1966 Oct;86(10):976-9. doi: 10.1248/yakushi1947.86.10_976.
3
Magnolamine and related compounds. IV. An alternative synthesis of D(-) and L(+)-N-methylcoclaurine.木兰胺及相关化合物。IV. D(-)和L(+) - N - 甲基去甲乌药碱的另一种合成方法。
Chem Pharm Bull (Tokyo). 1967 Sep;15(9):1283-6. doi: 10.1248/cpb.15.1283.

通过手性有机锂化合物的不对称取代实现双苄基异喹啉生物碱小檗胺的形式合成。

Formal synthesis of the bisbenzylisoquinoline alkaloid berbamunine by asymmetric substitution of chiral organolithium compounds.

作者信息

Gawley Robert E, Smith Gregory A

机构信息

Department of Chemistry and Biochemistry, University of Arkansas, Fayetteville, AR 72701, U.S.A.

出版信息

ARKIVOC. 2011 Jan 30;2011(Pt 5):167-179.

PMID:22003473
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3192450/
Abstract

Asymmetric alkylation of enantiomeric tetrahydroisoquinolyl oxazolines was achieved with 96-97% diastereoselectivity. Removal of the oxazoline chiral auxiliary and further transformations provide a straightforward synthesis of the two synthetic intermediates that were previously synthesized by resolution, and which comprise a formal synthesis of berbamunine by Ullman coupling.

摘要

对映体四氢异喹啉基恶唑啉的不对称烷基化反应以96 - 97%的非对映选择性实现。恶唑啉手性辅助基团的去除及进一步转化提供了两种合成中间体的直接合成方法，这两种中间体此前是通过拆分合成的，且通过乌尔曼偶联构成了小檗胺的形式合成。