Concise total syntheses of (-)-jorunnamycin A and (-)-jorumycin enabled by asymmetric catalysis

被引：83

作者：

Welin, Eric R. ^{[1
]}

Ngamnithipom, Aurapat ^{[1
]}

Klatte, Max ^{[1
]}

Lapointe, Guillaume ^{[1
]}

Pototschnig, Gerit M. ^{[1
]}

McDermott, Martina S. J. ^{[2
]}

Conklin, Dylan ^{[2
]}

Gilmore, Christopher D. ^{[1
]}

Tadross, Pamela M. ^{[1
]}

Haley, Christopher K. ^{[1
]}

Negoro, Kenji ^{[1
]}

Glibstrup, Emil ^{[1
]}

Grunanger, Christian U. ^{[1
]}

Allan, Kevin M. ^{[1
]}

Virgil, Scott C. ^{[1
]}

Slamon, Dennis J. ^{[2
]}

Stoltz, Brian M. ^{[1
]}

机构：

[1] CALTECH, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

[2] Univ Calif Los Angeles, Geffen Sch Med, Div Hematol Oncol, Dept Med, Los Angeles, CA 90095 USA

来源：

SCIENCE | 2019年 / 363卷 / 6424期

基金：

奥地利科学基金会; 瑞士国家科学基金会;

关键词：

HYDROGENATION; IDENTIFICATION; PHTHALASCIDIN; ISOQUINOLINES; QUINOLINES; COMPLEXES; JORUMYCIN; COMPOUND; PRODUCTS; ANALOGS;

D O I：

10.1126/science.aav3421

中图分类号：

O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

The bis-tetrahydroisoquinoline (bis-THIQ) natural products have been studied intensively over the past four decades for their exceptionally potent anticancer activity, in addition to strong Gram-positive and Gram-negative antibiotic character. Synthetic strategies toward these complex polycyclic compounds have relied heavily on electrophilic aromatic chemistry, such as the Pictet-Spengler reaction, that mimics their biosynthetic pathways. Herein, we report an approach to two bis-THIQ natural products, jorunnamycin A and jorumycin, that instead harnesses the power of modern transition-metal catalysis for the three major bond-forming events and proceeds with high efficiency (15 and 16 steps, respectively). By breaking from biomimicry, this strategy allows for the preparation of a more diverse set of nonnatural analogs.

引用

页码：270 / +

页数：138

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