A Unified Strategy for the Enantiospecific Total Synthesis of Delavatine A and Formal Synthesis of Incarviatone A

被引：22

作者：

Palani, Vignesh ^{[1
]}

Hugelshofer, Cedric L. ^{[1
]}

Sarpong, Richmond ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 36期

基金：

瑞士国家科学基金会; 美国国家科学基金会;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; DIELS-ALDER REACTION; COUPLING REACTIONS; MONOAMINE-OXIDASE; REGIOSELECTIVE SYNTHESIS; INCARVILLEA-DELAVAYI; HALOGENATED NITROGEN; BIOMIMETIC SYNTHESIS; NATURAL-PRODUCTS; 3,5-DIBROMO-2-PYRONE;

D O I：

10.1021/jacs.9b07693

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe a symmetry-inspired synthetic approach that has enabled a short synthesis of delavatine A and a formal synthesis of incarviatone A, which are two likely biosynthetically related natural products. The indane core of these natural products was constructed through a cascade sequence involving five transformations that occur in a single pot. Leveraging symmetry has allowed us to trace both natural products back to a versatile building block, 3,5-dibromo-2-pyrone, and studies related to site-selective cross-coupling of this polyhalogenated heterocycle are described. In addition, our strategy gave access to a putative biogenetic precursor, from which the syntheses of both natural products were attempted.

引用

页码：14421 / 14432

页数：12

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