Catalytic Z-Selective Cross-Metathesis in Complex Molecule Synthesis: A Convergent Stereoselective Route to Disorazole C1

被引：58

作者：

Speed, Alexander W. H. ^{[1
]}

Mann, Tyler J. ^{[1
]}

O'Brien, Robert V. ^{[1
]}

Schrock, Richard R. ^{[2
]}

Hoveyda, Amir H. ^{[1
]}

机构：

[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA

[2] MIT, Dept Chem, Cambridge, MA 02139 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 46期

关键词：

OLEFIN METATHESIS; MIXED ANHYDRIDE; ESTERIFICATION; ALLYLATION; OXIDATION; REAGENT;

D O I：

10.1021/ja509973r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convergent diastereo- and enantioselective total synthesis of anticancer and antifungal macrocydic natural product disorazole C-1 is reported. The central feature of the successful route is the application of catalytic Z-selective cross-metathesis (CM). Specifically, we illustrate that catalyst-controlled stereoselective CM can be performed to afford structurally complex Z-alkenyl-B(pin) as well as Z-alkenyl iodide compounds reliably, efficiently, and with high selectivity (pin = pinacolato). The resulting intermediates are then joined in a single-step operation through catalytic inter- and intramolecular cross-coupling to furnish the desired 30-membered ring macrocycle containing the critical (Z,Z,E)-triene moieties.

引用

页码：16136 / 16139

页数：4

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