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.
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页码：1 / 18
页数：18
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