Short, Divergent, and Enantioselective Total Synthesis of Bioactive ent-Pimaranes

被引：7

作者：

Plangger, Immanuel ^{[1
]}

Wurst, Klaus ^{[2
]}

Magauer, Thomas ^{[1
]}

机构：

[1] Leopold Franzens Univ Innsbruck, Inst Organ Chem, Ctr Mol Biosci, A-6020 Innsbruck, Austria

[2] Leopold Franzens Univ Innsbruck, Inst Gen Inorgan & Theoret Chem, A-6020 Innsbruck, Austria

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 39期

基金：

欧洲研究理事会;

关键词：

BIOGENETIC-TYPE SYNTHESIS; ASYMMETRIC DIHYDROXYLATION; LIGAND CLASS; DITERPENOIDS; INTERMEDIATE; REDUCTION; OXIDATION; ETHERS;

D O I：

10.1021/acs.orglett.2c02843

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present the first total synthesis of eight ent-pimaranes via a short and enantioselective route (11-16 steps). Key features of the divergent synthesis are a Sharpless asymmetric dihydroxylation, a Bronsted acid catalyzed cationic bicyclization, and a mild Rh-catalyzed arene hydrogenation for rapid access to a late synthetic branching point. From there on, selective functional group manipulations enable the synthesis of ent-pimaranes bearing different modifications in the A- and C-rings.

引用

页码：7151 / 7156

页数：6

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