Concise asymmetric total syntheses of (-)-nuciferol, (-)-nuciferal, and (-)-dihydrocurcumene via Rh(I)-catalyzed boronic acid addition

被引：7

作者：

Pal, Souvik ^{[1
]}

Khatua, Arindam ^{[1
]}

Das, Mrinal K. ^{[1
,4
]}

Bisai, Vishnumaya ^{[1
,2
,3
]}

机构：

[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, Madhya Pradesh, India

[2] Indian Inst Sci Educ & Res Tirupati, Dept Chem, Tirupati 462066, Andhra Pradesh, India

[3] Indian Inst Sci Educ & Res Berhampur, Dept Chem, Berhampur 462066, Odisha, India

[4] Univ Kalyani, Dept Chem, Karimpur Pannadevi Coll, Nadia 741152, W Bengal, India

来源：

TETRAHEDRON LETTERS | 2021年 / 65卷

关键词：

(E)-Crotonate; p-Tolylboronic acid; Rh(I)-catalyzed; Catalytic asymmetric; Bisabolane sesquiterpenes;

D O I：

10.1016/j.tetlet.2020.152790

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general catalytic asymmetric total synthesis of aromatic bisabolane sesquiterpenes, (-)-nuciferol (ent-1c), (-)-nuciferal (ent-1d), and (-)-dihydrocurcumene (ent-1h) have been achieved in 5-6 steps in high chemical yields from commercially available (E)-ethylcrotonate. A key catalytic enantioselective boronic acid addition onto (E)-crotonate in the presence of Rh(I)-(S)-BINAP afforded enantioenriched product with benzylic stereogenic center in 93% yield with up to >99% ee. (C) 2021 Elsevier Ltd. All rights reserved.

引用

页数：4

共 25 条

[1] Catalytic Enantioselective β-Alkylation of α,β-Unsaturated Aldehydes by Combination of Transition-Metal- and Aminocatalysis: Total Synthesis of Bisabolane Sesquiterpenes [J].

Afewerki, Samson ;

Breistein, Palle ;

Pirttila, Kristian ;

Deiana, Luca ;

Dziedzic, Pawel ;

Ibrahem, Ismail ;

Cordova, Armando .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (32) :8784-8788

[2] Iridium- Catalyzed Asymmetric Hydrogenation of 3,3-Disubstituted Allylic Alcohols in Ethereal Solvents [J].

Bernasconi, Maurizio ;

Ramella, Vincenzo ;

Tosatti, Paolo ;

Pfaltz, Andreas .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (09) :2440-2444

[3] POLYACETYLENIC COMPOUNDS .243. CONSTITUENTS OF COREOPSIS-PARVIFOLIA BLAKE [J].

BOHLMANN, F ;

ZDERO, C .

CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (02) :468-473

[4] First enantiospecific synthesis of (-)-parvifoline and (-)-curcuquinone [J].

Chavan, Subhash P. ;

Thakkar, Mahesh ;

Jogdand, Ganesh F. ;

Kalkote, Uttam R. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (23) :8986-8988

[5]

Du ZT, 2004, J CHEM RES, P427

[6] Versatile synthesis of cadalene and iso-cadalene from himachalene mixtures: Evidence and application of unprecedented rearrangements [J].

El Had, Mustapha Ait ;

Oukhrib, Abdelouahd ;

Zaki, Mohamed ;

Urrutigoity, Martine ;

Benharref, Ahmed ;

Chauvin, Remi .

CHINESE CHEMICAL LETTERS, 2020, 31 (07) :1851-1854

[7]

Fuganti C., 1999, J CHEM SCI PERKIN T, V58, P279

[8] Acetylcholinesterase Inhibitory Activity of Volatile Oil from Peltophorum dasyrachis Kurz ex Bakar (Yellow Batai) and Bisabolane-Type Sesquiterpenoids [J].

Fujiwara, Mai ;

Yagi, Nobuo ;

Miyazawa, Mitsuo .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (05) :2824-2829

[9] SESQUITERPENES FROM PEREZIA-LONGIFOLIA [J].

GARCIA, E ;

MENDOZA, V ;

GUZMAN, JA .

JOURNAL OF NATURAL PRODUCTS, 1988, 51 (01) :150-151

[10] PEREZONE AND RELATED SESQUITERPENES FROM PARVIFOLINE [J].

GARCIA, E ;

MENDOZA, V ;

GUZMAN, A .

JOURNAL OF NATURAL PRODUCTS, 1987, 50 (06) :1055-1058

← 1 2 3 →