Total Synthesis of (R)-Sarkomycin Methyl Ester via Regioselective Intermolecular Pauson-Khand Reaction and Iridium-Catalyzed Asymmetric Isomerization

被引：22

作者：

Cabre, Albert ^{[1
,2
]}

Khaizourane, Helea ^{[1
]}

Garcon, Marti ^{[1
,2
]}

Verdaguer, Xavier ^{[1
,2
]}

Riera, Antoni ^{[1
,2
]}

机构：

[1] Barcelona Inst Sci & Technol, Inst Res Biomed IRB Barcelona, Baldiri Reixac 10, E-08028 Barcelona, Spain

[2] Univ Barcelona, Dept Quim Inorgan & Organ, Seccio Organ, Marti i Franques 1, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 13期

关键词：

FORMAL TOTAL-SYNTHESIS; DIELS-ALDER REACTIONS; ALLYLIC ALCOHOLS; SELECTIVE ISOMERIZATION; SARKOMYCIN; CYCLIZATION; SARCOMYCIN; CONVERSION; ACCESS; ADDUCT;

D O I：

10.1021/acs.orglett.8b01525

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new five step enantioselective synthesis of (R)-sarkomycin methyl ester is described. The cyclopentane scaffold was built by a regioselective intermolecular Pauson-Khand reaction. Enantioselectivity was introduced by a novel Ir-catalyzed isomerization reaction. The last steps involved a catalytic hydrogenation of the exocylic double bond, followed by the deprotection and elimination of the amino group. This route is the shortest enantioselective synthesis of this antibiotic reported to date.

引用

页码：3953 / 3957

页数：5

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