Four-Step Total Synthesis of (+)-Yaoshanenolides A and B

被引：17

作者：

Thorat, Sagar S. ^{[1
,2
]}

Palange, Megha N. ^{[1
,2
]}

Kontham, Ravindar ^{[1
,2
]}

机构：

[1] CSIR, Natl Chem Lab, Div Organ Chem, Dr Homi Bhabha Rd, Pune 411008, Maharashtra, India

[2] Acad Sci & Innovat Res AcSIR, New Delhi 110025, India

来源：

ACS OMEGA | 2018年 / 3卷 / 06期

关键词：

BAYLIS-HILLMAN REACTION; CORE; YAOSHANENOLIDES; CHEMISTRY; CATALYST; ANALOGS;

D O I：

10.1021/acsomega.8b00701

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly concise bioinspired four-step total synthesis of yaoshanenolides A and B possessing tricyclic spirolactone with an unusual 5'H-spiro-[bicyclo[2.2.2]-oct[2] ene-7,2'-furan]-5'-one scaffold is reported. This synthesis features high-yielding aldol-type addition of gamma-butyrolactone on to the aldehyde, exocyclic olefination of lactone derivative using Eschenmoser's salt, and highly facial-and endo-selective [4 + 2]-cycloaddition of fully functionalized 5-methylene-2(5H)-furanone with natural R-(-)-alpha-phellandrene. The approach allows access to yaoshanenolides A and B in four linear steps in 11 and 13% overall yield.

引用

页码：7036 / 7045

页数：10

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