Silver-catalyzed benzannulation, part 2: total synthesis of (1R,4S,11S)-8,19-dihydroxyserrulat-14-ene and (1R,4S,11S)-8-hydroxyserrulat-14-en-19-oic acid

被引：0

作者：

Ozerskaya, Anastasia, V ^{[1
,2
]}

Larkina, Mariia S. ^{[1
,3
]}

Podrezova, Ekaterina, V ^{[1
]}

Svitich, Dmitrii Yu ^{[1
]}

Yusubova, Roza Ya ^{[1
]}

Zhdankin, Viktor V. ^{[4
]}

Yusubov, Mekhman S. ^{[1
,3
]}

机构：

[1] Tomsk Polytech Univ, Tomsk 634050, Russia

[2] Fed Siberian Res Clin Ctr, Krasnoyarsk 660037, Russia

[3] Siberian State Med Univ, Tomsk 634050, Russia

[4] Univ Minnesota Duluth, Dept Chem & Biochem, Duluth, MN 55812 USA

来源：

ARKIVOC | 2022年

关键词：

Benzannulation; serrulatane; 5-alkoxy-1; 5-enynes; 6-endo-dig cyclisation; tetrahydronaphthalene; OXIDATION; ALCOHOLS;

D O I：

10.24820/ark.5550190.p011.815

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This paper reports the total synthesis of the serrulatane natural products (1R,4S,11S)-8,19-dihydroxyserrulat-14-ene (5.0% yield) and (1R,4S,11S)-8-hydroxyserrulat-14-en-19-oic acid (3.8% yield) via a silver-catalyzed 6-endo-dig benzannulation of an (-)-isopulegol derived ene-yne-ol in 17 steps. Analysis of the spectroscopic data as well as the specific rotations allowed for the confirmation of the stereochemistry at C1, C4 and C11 as (1R,4S,11S) for both natural products 8,19-dihydroxyserrulat-14-ene and 8-hydroxyserrulat-14-en-19-oic acid that were reported from the Australian desert plant, Eremophila neglecta.

引用

页码：1 / 18

页数：18

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