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

[1] A concise synthetic route to optically active cis-β,γ-disubstituted-γ-butyrolactones via tandem Michael-MPV reaction:: new total synthesis of (-)-cis-whisky lactone and (-)-cis-cognac lactone
Ozeki, M
Hashimoto, D
Nishide, K
Kajimoto, T
Node, M
TETRAHEDRON-ASYMMETRY, 2005, 16 (09) : 1663 - 1671
[2] SYNTHESIS OF (+)-TRANS-WHISKEY LACTONE, (-)-CIS-WHISKEY LACTONE, (+)-COGNAC LACTONE AND (+)-ELDANOLIDE
EBATA, T
MATSUMOTO, K
YOSHIKOSHI, H
KOSEKI, K
KAWAKAMI, H
OKANO, K
MATSUSHITA, H
HETEROCYCLES, 1993, 36 (05) : 1017 - 1026
[3] A concise asymmetric synthesis of (-)-trans-aerangis lactone
Pandey, Rachana
Prakash, Ranjana
CANADIAN JOURNAL OF CHEMISTRY, 2018, 96 (12) : 1061 - 1063
[4] Radical cyclization route to the stereoselective synthesis of (+)-trans-cognac lactone and (+)-trans-aerangis lactone
Sabitha, Gowravaram
Bhikshapathi, M.
Yadav, J. S.
SYNTHETIC COMMUNICATIONS, 2007, 37 (4-6) : 559 - 567
[5] SYNTHESIS OF (+/-)-CIS-WHISKEY LACTONE
EBATA, T
KAWAKAMI, H
MATSUMOTO, K
KOSEKI, K
OKANO, K
MATSUSHITA, H
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1993, 57 (03) : 515 - 516
[6] CONCISE ENANTIOSPECIFIC SYNTHESES OF (+)-ELDANOLIDE AND (-)-CIS-WHISKY LACTONE
SUZUKI, Y
MORI, W
ISHIZONE, H
NAITO, K
HONDA, T
TETRAHEDRON LETTERS, 1992, 33 (34) : 4931 - 4932
[7] Asymmetric Synthesis of (+)-trans-Aerangis Lactone
Kim, Aejin
Sharma, Satyasheel
Kwak, Jong Hwan
Kim, In Su
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (01) : 75 - 78
[8] Synthesis of (+/-)-methylenolactocin and (+/-)-trans cognac lactone
Ohta, Y
Okamoto, T
Tamura, M
Doe, M
Morimoto, Y
Yoshihara, K
Kinoshita, T
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (02) : 485 - 487
[9] Synthesis of natural fragrant molecules cis-3-methyl-4-decanolide and aerangis lactone.: General enantioselective routes to β,γ-cis-disubstituted γ-lactones and γ,δ-cis-disubstituted δ-lactones
Wu, YK
Shen, X
Tang, CJ
Chen, ZL
Hu, Q
Shi, W
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11): : 3802 - 3810
[10] SYNTHESIS OF (+)-TRANS-WHISKEY LACTONE, (+)-TRANS-COGNAC LACTONE AND (+)-ELDANOLIDE
EBATA, T
MATSUMOTO, K
YOSHIKOSHI, H
KOSEKI, K
KAWAKAMI, H
MATSUSHITA, H
HETEROCYCLES, 1990, 31 (09) : 1585 - 1588

← 1 2 3 4 5 →