A Concise Route to Dihydrobenzo[b]furans: Formal Total Synthesis of (+)-Lithospermic Acid

被引：57

作者：

Fischer, Joshua ^{[1
]}

Savage, G. Paul ^{[2
]}

Coster, Mark J. ^{[1
]}

机构：

[1] Griffith Univ, Eskitis Inst Cell & Mol Therapies, Nathan, Qld 4111, Australia

[2] CSIRO Mat Sci & Engn, Clayton, Vic 3169, Australia

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 13期

基金：

澳大利亚研究理事会;

关键词：

CELL-SUSPENSION CULTURES; C-H INSERTION; SALVIA-MILTIORRHIZA; ALPHA; BETA-UNSATURATED ESTERS; CARBONYLATIVE ANNULATION; LITHOSPERMUM-RUDERALE; ASYMMETRIC-SYNTHESIS; CONJUGATE REDUCTION; PALLADIUM-THIOUREA; DERIVATIVES;

D O I：

10.1021/ol201130h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A sequence of Sonogashira coupling, Pd(II)-catalyzed carbonylative annulation, and benzofuran reduction (Mg, MeOH, NH(4)Cl) provides a convergent and modular synthetic route to trans-2-aryl-2,3-dihydrobenzo[b]furan-3-carboxylates, which are a structural feature of numerous biologically active natural products. This versatile strategy was applied to the formal total synthesis of the anti-HIV natural product (+)-lithospermic acid.

引用

页码：3376 / 3379

页数：4

共 50 条

[41] Enantioselective total synthesis of iso-cladospolide B, cladospolide C and cladospolide B from tartaric acid [J].

Prasad, Kavirayani R. ;

Gandi, Vasudeva Rao .

TETRAHEDRON-ASYMMETRY, 2011, 22 (05) :499-505

[42] Total synthesis of decytospolides A, B and a formal synthesis of aspergillide A starting from D-mannitol via tandem/domino reactions by Grubb's catalysts [J].

Kammari, Bal Raju ;

Bejjanki, Naveen Kumar ;

Kommu, Nagaiah .

TETRAHEDRON-ASYMMETRY, 2015, 26 (5-6) :296-303

[43] Acid-Catalyzed Ring-Opening Cyclization of Spirocyclopropanes for the Construction of a 2-Arylbenzofuran Skeleton: Total Synthesis of Cuspidan B [J].

Nambu, Hisanori ;

Ono, Naoki ;

Yakura, Takayuki .

SYNTHESIS-STUTTGART, 2016, 48 (12) :1892-1901

[44] A general synthetic approach to the amnesic shellfish toxins: total synthesis of (-)-isodomoic acid B, (-)-isodomoic acid E and (-)-isodomoic acid F [J].

Lemiere, Gilles ;

Sedehizadeh, Simon ;

Toueg, Julie ;

Fleary-Roberts, Nadia ;

Clayden, Jonathan .

CHEMICAL COMMUNICATIONS, 2011, 47 (13) :3745-3747

[45] Concise Synthesis of (+)-allo-Kainic Acid via MgI2-Mediated Tandem Aziridine Ring Opening-Formal [3+2] Cycloaddition [J].

Arena, Giada ;

Chen, C. Chun ;

Leonori, Daniele ;

Aggarwal, Varinder K. .

ORGANIC LETTERS, 2013, 15 (16) :4250-4253

[46] Divergent Synthetic Route to Oxidized Benzofulvene Sesquiterpenoids: Protecting-Group-Free Total Synthesis of Nicotianasesterpenes A, B, and a Polygonum Sesquiterpenoid [J].

Jeong, Myeonggyo ;

Lee, Hyunkee ;

Kim, Gibeom ;

Jo, Jeyun ;

Chang, Jae Won ;

Jung, Jee H. ;

Suh, Young-Ger ;

Yun, Hwayoung .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (39) :6714-6719

[47] Intramolecular Alkynylogous Mukaiyama Aldol Reaction Starting from Bicyclic Alkanones Tethered to Alkynyl Esters: Formal Total Synthesis of (±)-Hamigeran B [J].

Miesch, Laurence ;

Welsch, Tania ;

Rietsch, Vincent ;

Miesch, Michel .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (17) :4394-4401

[48] Acid-induced Favorskii-type Reaction: Regiocontrolled Elimination of Acyloin Mesylates Leading to α,β-Unsaturated Ketones and Application to Formal Total Synthesis of (R)-Muscone from Racemic Muscone [J].

Ashida, Yuichiro ;

Tanaka, Akihiro ;

Hosomi, Kohei ;

Nakamura, Atsushi ;

Misaki, Tomonori ;

Nakatsuji, Hidefumi ;

Tanabe, Yoo .

CHEMISTRYSELECT, 2016, 1 (12) :3215-3218

[49] Asymmetric synthesis of abietane diterpenoids via B-alkyl Suzuki-Miyaura coupling.: Formal total asymmetric synthesis of 12-deoxyroyleanone and cryptoquinone [J].

Yajima, Arata ;

Yamaguchi, Ayumi ;

Saitou, Fumihiro ;

Nukada, Tomoo ;

Yabuta, Goro .

TETRAHEDRON, 2007, 63 (05) :1080-1084

[50] Stereoselective synthesis of C-6 substituted pipecolic acid derivatives. Formal synthesis of (+)-indolizidine 167B and (+)-indolizidine 209D [J].

Carbonnel, S ;

Troin, Y .

HETEROCYCLES, 2002, 57 (10) :1807-1830

← 1 2 3 4 5 →