Concise Total Synthesis of (-)-cis-Aerangis Lactone and (-)-cis-Cognac Lactone

被引：11

作者：

Yadav, Jhillu S. ^{[1
]}

Rao, Ragam Nageshwar ^{[1
]}

Kumar, Begari Prem ^{[1
]}

Somaiah, Ragam ^{[1
]}

Ravindar, Kontham ^{[1
]}

Reddy, Basi V. Subba ^{[1
]}

Al Ghamdi, Ahamad Al Khazim ^{[2
]}

机构：

[1] Indian Inst Chem Technol, Organ Chem Div 1, Hyderabad 500007, Andhra Pradesh, India

[2] King Saud Univ, Riyadh 11451, Saudi Arabia

来源：

SYNTHESIS-STUTTGART | 2011年 / 19期

关键词：

lactones; Wittig olefination; Sharpless asymmetric epoxidation; intramolecular hydride transfer; syn-aldol; GAMMA-BUTYROLACTONES; (+)-TRANS-WHISKEY LACTONE; STEREOSELECTIVE-SYNTHESIS; ROUTE; (+)-ELDANOLIDE; ENANTIOMERS; CYCLIZATION; RESOLUTION;

D O I：

10.1055/s-0030-1260190

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and concise stereoselective total synthesis of naturally occurring (-)-cis-aerangis lactone and (-)-cis-cognac lactone is described. The Sharpless asymmetric epoxidation of a primary allylic alcohol and TBSOTf-mediated intramolecular hydride transfer of a chiral epoxy alcohol have been successfully utilized for the construction of a key precursor with syn-aldol stereochemistry using a non-aldol pathway.

引用

页码：3168 / 3172

页数：5

共 50 条

[11] A chemoenzymatic synthesis of both enantiomers of a cis-lignan lactone
Chênevert, R
Rose, YS
TETRAHEDRON-ASYMMETRY, 1998, 9 (16) : 2827 - 2831
[12] Enantio- and diastereoselective hetero-Diels-Alder reactions between 4-methyl-substituted Rawal's diene and aldehydes catalyzed by chiral dirhodium(II) carboxamidates: catalytic asymmetric synthesis of (-)-cis-aerangis lactone
Watanabe, Yudai
Shimada, Naoyuki
Anada, Masahiro
Hashimoto, Shunichi
TETRAHEDRON-ASYMMETRY, 2014, 25 (01) : 63 - 73
[13] THE REACTION OF CIS-2-ALPHA-CARBOXYETHYLCYCLOPENTANOL LACTONE
TANAKA, T
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1962, 35 (11) : 1890 - 1894
[14] SESQUITERPENE LACTONE TOTAL SYNTHESIS
GRIECO, PA
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1977, 173 (MAR20): : 51 - 51
[15] A concise and diastereoselective total synthesis of cis and trans-pterocarpans
Jiménez-González, L
Alvarez-Corral, M
Muñoz-Dorado, M
Rodríguez-García, I
CHEMICAL COMMUNICATIONS, 2005, (21) : 2689 - 2691
[16] A simple route to the syntheses of both enantiomers of trans-oak lactone and (+)-cis-oak lactone
Ghosh, Manju
Bose, Sritama
Ghosh, Subrata
TETRAHEDRON LETTERS, 2008, 49 (37) : 5424 - 5426
[17] Synthesis of γ- and δ-Lactone Natural Products by Employing a trans-cis Isomerization/Lactonization Strategy
Ono, Machiko
Kato, Keisuke
Akita, Hiroyuki
CHEMICAL & PHARMACEUTICAL BULLETIN, 2013, 61 (04) : 464 - 470
[18] SYNTHESIS AND ALKYLATION OF CIS-3-ALPHA-HYDROXYISOPROPYLINDANONE-2-CARBOXYLIC ACID LACTONE
CAMPAIGNE, E
FRIERSON, MR
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (02) : 235 - 237
[19] Concise total synthesis of (+)-brefeldin A:: A combined β-lactone/cross-metathesis-based strategy
Wang, YC
Romo, D
ORGANIC LETTERS, 2002, 4 (19) : 3231 - 3234
[20] Cyclopentane construction via β-lactone intermediates:: Application to a concise total synthesis of (+)-brefeldin A.
Wang, YC
Romo, D
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 221 : U180 - U180

← 1 2 3 4 5 →